1H-indole-3-carboxylic acid [CAS 771-50-6; InChIKey KMAKOBLIOCQGJP-UHFFFAOYSA-N; Reaxys, All

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Date

56 reactions in Reaxys

2016-03-08 21h:00m:09s (EST)

O OH

1. Query NH

Search as: As drawn

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NH

NH O

O

OH O

Rx-ID: 28766977 View in Reaxys 1/56 Yield

Conditions & References

95 %

Stage 1: With lithium tert-butylate in DMFA, Time= 24h, T= 100 °C , p= 760.051Torr Stage 2: With hydrochlorid acid in water, DMFA, Reagent/catalyst, Solvent Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu; Organic Letters; vol. 14; nb. 20; (2012); p. 5326 - 5329,4 View in Reaxys

95 %

Representative procedure for the direct C-H carboxylation of indole derivatives 1a-p In a dried two-necked test tube was charged with LiOtBu (160 mg, 2.00 mmol) and indole 1a (23.4 mg, 0.4 mmol). The reaction vessel was evacuated under high vacuum and the atmosphere was replace with a balloon of CO2. Then DMF (2 mL) was added and the mixture was stirred for 24 h at 100°C. Then the result mixture was cooled and carefully quenched with a solution of HCl (2 N) and extracted with EtOAc (5x). The combined organic layers were washed with water (2x), brine (1x) and dry over MgSO4. The dried organics were concentrated under reduce pressure and the residue was purified by preparative TLC (hexane:acetone = 1:1) to afford the desired product 2a (153.0 mg, 95percent) as a white solid.

With lithium tert-butylate in DMFA, Time= 24h, T= 100 °C , p= 760.051Torr , Reagent/catalyst, Time Yoo, Woo-Jin; Nguyen, Thanh V. Q.; Guiteras Capdevila, Montse; Kobayashi, Shu; Heterocycles; vol. 90; nb. 2; (2015); p. 1196 - 1204 View in Reaxys

37 %

3.6. Typical procedure for the carboxylation of indoles (entry 1 in Table 1) General procedure: In a 50 mL autoclave equipped with a glass inner tube and a magnetic stirring bar were charged indole 1a (d 1.05; 125 mL, 1.00 mmol), Me2AlCl (1.0 M solution in hexane; 1.0 mL, 1.0 mmol), toluene (1.0 mL) under nitrogen atmosphere, and the apparatus was purged with CO2 by repeated pressurization and subsequent expansion, the final pressure being adjusted to 3.0 MPa. After the mixture was stirred at 80 °C for 3 h, the reactor was allowed to cool to room temperature and depressurized. The reaction mixture was quenched with 2 M HCl and the aqueous layer was extracted with ethyl acetate. The combined organic layer was extracted with 0.5M Na2CO3 and the extract was acidified by the addition of concentrated HCl to liberate the free carboxylic acid, which was extracted with ethyl acetate.

The extract was dried over MgSO4 and evaporated to leave a residue, which was purified by column chromatography with chloroform-ethyl acetate (1:1) as an eluent to give acid 2a as crystals (168 mg, 96percent). The carboxylation of other indoles was conducted by a similar procedure. The crude product was routinely purified by column chromatography using chloroform-ethyl acetate (1:1) or chloroform-ethyl acetate (1:1) containing 1percent (v/v) of acetic acid as an eluent. See Tables 1 and 2 for the reaction conditions and product yields.

With dimethylaluminum chloride in hexane, toluene, Time= 3h, T= 80 °C , p= 22502.3Torr , Autoclave, Temperature Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745 View in Reaxys

28 %

With dimethylaluminum chloride in hexane, toluene, Time= 3h, T= 20 °C , p= 22502.3Torr , Friedel-Crafts reaction, regioselective reaction Nemoto, Koji; Onozawa, Satoru; Egusa, Naoki; Morohashi, Naoya; Hattori, Tetsutaro; Tetrahedron Letters; vol.

50; nb. 31; (2009); p. 4512 - 4514 View in Reaxys

NH

N

OH

OH

O

O

Rx-ID: 41658422 View in Reaxys 2/56

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Yield

Conditions & References

98 %

3.8. Deprotection of 1-benzylindole 8a To a solution of 1-benzylindole 8a (25.1 mg, 0.100 mmol) in benzene (1.0 mL) was added AlCl3 (66.7 mg, 0.500 mmol) at -10 °C, and the mixture was allowed to warm to room temperature. After stirring at room temperature for 18 h, the mixture was quenched with water and the aqueous layer was extracted with chloroform. The combined organic layer was extracted with 0.5 M Na2CO3 and the extract was acidified by the addition of concentrated HCl to liberate the free acid, which was extracted with chloroform. The extract was dried over MgSO4 and evaporated to leave a residue, which was purified by TLC with chloroform-ethylacetate (1:1) as a developer to give 6a (15.8 mg, 98percent).

With AlCl3, aluminium chloride in benzene, Time= 18h, T= -10 - 20 °C Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745 View in Reaxys

NH

Si N

OH O

OH O

Rx-ID: 41658461 View in Reaxys 3/56 Yield

Conditions & References

95 %

3.7. Deprotection of 1-triisopropylsilylindole 7a To a solution of 1-triisopropylsilylindole 7a (31.7 mg, 0.100 mmol) in THF (1.0 mL) was added TBAF (1.0 M solution in THF; 1.0 mL, 1.0 mmol), and the mixture was stirred at room temperature for 18 h. The reaction was quenched by the addition of water and the aqueous layer was extracted with chloroform. The combined organic layer was dried over MgSO4 and evaporated to leave a residue, which was purified by TLC with chloroform-ethylacetate (1:1) as a developer to give deprotected indole 6a (15.3 mg, 95percent).

With tetrabutyl ammonium fluoride in tetrahydrofuran, Time= 18h, T= 20 °C Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745 View in Reaxys

NH

NH

OH

N

O

Rx-ID: 92363 View in Reaxys 4/56 Yield 50 %

Conditions & References With phosphate buffer, Time= 144h, T= 30 °C , rhodococcus rhodocrous AJ270, pH 7.0 Meth-Cohn, Otto; Wang, Mei-Xiang; Tetrahedron Letters; vol. 36; nb. 52; (1995); p. 9561 - 9564 View in Reaxys

50.4 %

With potassium phosphate buffer, Time= 144h, T= 30 °C , Rhodococcus sp. AJ270 cells Meth-Cohn, Otto; Wang, Mei-Xiang; Journal of the Chemical Society - Perkin Transactions 1; nb. 8; (1997); p. 1099 - 1104 View in Reaxys

38 %

With phosphate buffer, Time= 72h, immobilized nitrilase from Rhodococcus sp.

Klempier; De Raadt; Faber; Grieng; Tetrahedron Letters; vol. 32; nb. 3; (1991); p. 341 - 344 View in Reaxys With potassium hydroxide Majima et al.; Chemische Berichte; vol. 57; (1924); p. 1456,1462

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View in Reaxys With sodium hydroxide Shaw et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 1171,1176 View in Reaxys Stage 1: With sodium hydroxide Stage 2: With hydrogenchloride in water Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497 View in Reaxys

O NH

N

OH

OH

O

O

Rx-ID: 2831716 View in Reaxys 5/56 Yield

Conditions & References

95 %

With sodium hydroxide in ethanol, water, Time= 4h, T= 70 °C Itahara, Toshio; Chemistry Letters; (1982); p. 1151 - 1152 View in Reaxys

NH

NH

O

OH

O

O

Rx-ID: 9641784 View in Reaxys 6/56 Yield

Conditions & References

61 %

With sodium hydroxide in isopropyl alcohol, Time= 1h, T= 85 - 90 °C Zaletova, Janka; Dzurilla, Milan; Kutschy, Peter; Pazdera, Pavel; Kovacik, Vladimir; Aldoelfi, Juraj; Bekesova, Slavka; Collection of Czechoslovak Chemical Communications; vol. 69; nb. 2; (2004); p. 453 - 460 View in Reaxys With water, sodium hydroxide, Time= 3h, Inert atmosphere, Reflux Miles, Kelsey C.; Le, Chi; Stambuli, James P.; Chemistry--A European Journal; vol. 20; nb. 36; (2014); p. 11336 11339,4 View in Reaxys

NH

NH

F F O

F

OH O

Rx-ID: 261474 View in Reaxys 7/56 Yield

Conditions & References With potassium hydroxide Whalley; Journal of the Chemical Society; (1954); p. 1651 View in Reaxys With sodium hydroxide Hopkins, Corey R.; Czekaj, Mark; Kaye, Steven S.; Gao, Zhongli; Pribish, James; Pauls, Henry; Liang, Guyan; Sides, Keith; Cramer, Dona; Cairns, Jennifer; Luo, Yongyi; Lim, Heng-Keang; Vaz, Roy; Rebello, Sam; Maignan, Sebastian; Dupuy, Alain; Mathieu, Magali; Levell, Julian; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb.

11; (2005); p. 2734 - 2737

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View in Reaxys With sodium hydroxide, water, T= 50 °C Park, Chul Min; Kim, So Young; Park, Woo Kyu; Park, No Sang; Seong, Churl Min; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 14; (2008); p. 3844 - 3847 View in Reaxys With water, sodium hydroxide, Reflux Kumar, Dalip; Maruthi Kumar; Chang, Kuei-Hua; Shah, Kavita; European Journal of Medicinal Chemistry; vol. 45; nb. 10; (2010); p. 4664 - 4668 View in Reaxys 2.47 g

With sodium hydroxide in water, T= 50 °C Wang, Yu; Haemaelaeinen, Antti; Tois, Jan; Franzen, Robert; Tetrahedron Asymmetry; vol. 21; nb. 19; (2010); p.

2376 - 2384 View in Reaxys

NH

NH

OH

O

O

Rx-ID: 1647447 View in Reaxys 8/56 Yield

Conditions & References With potassium hydroxide, potassium permanganate in ethanol, water, Time= 0.0833333h, T= 50 - 60 °C , Yield given Schallenberg, Juergen; Meyer, Eckart; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 38; nb. 1; (1983); p. 108 - 112 View in Reaxys Reaction Steps: 3 1: hydroxylamine hydrochloride; sodium acetate 2: acetic anhydride / acetic acid 3: sodium hydroxide With hydroxylamine hydrochloride, sodium acetate, acetic anhydride, sodium hydroxide in acetic acid Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497 View in Reaxys With anhydrous sodium pyrophosphate, bovine xanthine oxidase in aq. buffer, Time= 24h, T= 4 °C , Darkness Cao, Hongnan; Hall, James; Hille, Russ; Biochemistry; vol. 53; nb. 3; (2014); p. 533 - 541 View in Reaxys With fungal intracellular enzyme from cultural mycelium of fungus Daldinia eschscholzii IFB-TL01 from mantis Tenodera aridifolia guts, Time= 2h, T= 28 °C Lin, Li Ping; Yuan, Peng; Jiang, Nan; Mei, Ya Ning; Zhang, Wen Jing; Wu, Hui Min; Zhang, Ai Hua; Cao, Jiang Ming; Xiong, Zheng Xin; Lu, Ye; Tan, Ren Xiang; Organic Letters; vol. 17; nb. 11; (2015); p. 2610 - 2613 View in Reaxys

NH

NH

OH O

Rx-ID: 44397 View in Reaxys 9/56 Yield

Conditions & References With sodium, T= 190 - 200 °C , Einleiten von Kohlendioxyd in das Reaktionsgemisch Weissgerber; Chemische Berichte; vol. 43; (1910); p. 3526

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View in Reaxys With sodium, 1-methylnaphtalene, T= 190 - 200 °C , Einleiten von Kohlendioxyd in das Reaktionsgemisch Patent; Ges. f. Teerverwertung; DE230542; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 10; p. 356 View in Reaxys Reaction Steps: 2 1: dimethylformamide 2: aq. NaOH With sodium hydroxide in DMFA Hopkins, Corey R.; Czekaj, Mark; Kaye, Steven S.; Gao, Zhongli; Pribish, James; Pauls, Henry; Liang, Guyan; Sides, Keith; Cramer, Dona; Cairns, Jennifer; Luo, Yongyi; Lim, Heng-Keang; Vaz, Roy; Rebello, Sam; Maignan, Sebastian; Dupuy, Alain; Mathieu, Magali; Levell, Julian; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb.

11; (2005); p. 2734 - 2737 View in Reaxys Reaction Steps: 2 1: zinc chloride; hydrogen chloride; diethyl ether / Behandeln des Reaktionsgemisches mit Wasser.

2: aqueous KOH With hydrochlorid acid, potassium hydroxide, diethyl ether, zinc(II) chloride Whalley; Journal of the Chemical Society; (1954); p. 1651 View in Reaxys Reaction Steps: 2 1: zinc chloride; hydrogen chloride; diethyl ether / Behandeln des Reaktionsgemisches mit Wasser.

2: aqueous NaOH With hydrochlorid acid, sodium hydroxide, diethyl ether, zinc(II) chloride Whalley; Journal of the Chemical Society; (1954); p. 1651 View in Reaxys Reaction Steps: 4 1: phosphoryl chloride 2: hydroxylamine hydrochloride; sodium acetate 3: acetic anhydride / acetic acid 4: sodium hydroxide With hydroxylamine hydrochloride, sodium acetate, acetic anhydride, sodium hydroxide, phosphoryl chloride in acetic acid Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497 View in Reaxys Reaction Steps: 3 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -20 °C 1.2: 2 h 2.1: dimethylaluminum chloride / hexane; toluene / 3 h / 20 °C / 22502.3 Torr / |Autoclave 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C With n-butyllithium, tetrabutyl ammonium fluoride, dimethylaluminum chloride in tetrahydrofuran, hexane, toluene Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745 View in Reaxys Reaction Steps: 3 1.1: sodium hydride / DMFA; mineral oil / 0.5 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: dimethylaluminum chloride / hexane; toluene / 3 h / 20 °C / 22502.3 Torr / |Autoclave 3.1: AlCl3, aluminium chloride / benzene / 18 h / -10 - 20 °C With AlCl3, aluminium chloride, dimethylaluminum chloride, sodium hydride in hexane, DMFA, toluene, mineral oil, benzene

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Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745 View in Reaxys

O

NH

NH

OH K+ O–

OH O

Rx-ID: 9237776 View in Reaxys 10/56 Yield

Conditions & References

6.81 mmol

With resting-cells of Arthrobacter nicotianae FI1612, DL-threo-1,4-dimercapto-2,3-butanediol in methanol, phosphate buffer, Time= 6h, T= 20 °C , pH= 7.0 Yoshida, Toyokazu; Fujita, Kohei; Nagasawa, Toru; Bioscience, Biotechnology and Biochemistry; vol. 66; nb. 11; (2002); p. 2388 - 2394 View in Reaxys

–H

NH F F

2C

3

F

O

Na +

Sn

F

Cl

O–

HN

O

O–

Sn4+

Rx-ID: 27407266 View in Reaxys 11/56 Yield

Conditions & References

80 %

in benzene, anhyd. salt of ligand added to benzene soln. of Sn compd. (molar ratio 1.2:1); stirred at 40°C for 15 h; filtered; solvent removed gradially from filtrate under vac.; recrystd. from acetone-hexane; elem. anal.

Yin, Handong D.; Wang, Chuanhua; Ma, Chunlin; Wang, Daqi; Journal of Organometallic Chemistry; vol. 689; nb.

1; (2004); p. 246 - 251 ; (from Gmelin) View in Reaxys

F

NH

O

O

F

NH

F

F O F

OH

F

O

Rx-ID: 34442163 View in Reaxys 12/56 Yield

Conditions & References Stage 1: in N,N-dimethyl-formamide, Time= 3h, T= 0 °C Stage 2: With sodium hydroxide in N,N-dimethyl-formamide, Time= 12h, T= 100 °C Kumar, Dalip; Arun; MaruthiKumar; Acosta, Glen; Noel, Brett; Shah, Kavita; ChemMedChem; vol. 7; nb. 11; (2012); p. 1915 - 1920 View in Reaxys

NH

NH

N

OH

OH

O

Rx-ID: 36321599 View in Reaxys 13/56 Yield

Conditions & References Reaction Steps: 2 1: acetic anhydride / acetic acid 2: sodium hydroxide With acetic anhydride, sodium hydroxide in acetic acid Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497 View in Reaxys

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NH

indol-aldehyde-(3) OH O

Rx-ID: 5430449 View in Reaxys 14/56 Yield

Conditions & References With potassium permanganate, T= 50 - 60 °C Ellinger; Chemische Berichte; vol. 39; (1906); p. 2520 View in Reaxys

O

NH

N

OH O

Rx-ID: 20823808 View in Reaxys 15/56 Yield

Conditions & References Reaction Steps: 2 1: 37 percent / Pd(OAc)2, sodium peroxydisulfate / acetic acid / 7 h / Heating 2: 95 percent / NaOH / ethanol; H2O / 4 h / 70 °C With palladium diacetate, sodium hydroxide, sodium peroxodisulphate in ethanol, water, acetic acid Itahara, Toshio; Chemistry Letters; (1982); p. 1151 - 1152 View in Reaxys

NH

N OH O

Rx-ID: 41658409 View in Reaxys 16/56 Yield

Conditions & References Reaction Steps: 2 1: dimethylaluminum chloride / hexane; toluene / 3 h / 20 °C / 22502.3 Torr / |Autoclave 2: AlCl3, aluminium chloride / benzene / 18 h / -10 - 20 °C With AlCl3, aluminium chloride, dimethylaluminum chloride in hexane, toluene, benzene Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745 View in Reaxys

NH

Si N

OH O

Rx-ID: 41658460 View in Reaxys 17/56 Yield

Conditions & References Reaction Steps: 2 1: dimethylaluminum chloride / hexane; toluene / 3 h / 20 °C / 22502.3 Torr / |Autoclave 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C With tetrabutyl ammonium fluoride, dimethylaluminum chloride in tetrahydrofuran, hexane, toluene Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745 View in Reaxys

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NH

NH

O

NH

OH

OH O

Rx-ID: 44395 View in Reaxys 18/56 Yield

Conditions & References With sodium, T= 230 - 250 °C , im Kohlendioxyd-Strom; zuletzt bei 300grad Zatti; Ferratini; Chemische Berichte; vol. 23; (1890); p. 2296; Gazzetta Chimica Italiana; vol. 20; (1890); p. 707 View in Reaxys

NH

NH

Cl

OH

O

O

Rx-ID: 118731 View in Reaxys 19/56 Yield

Conditions & References With sodium hydrogencarbonate Peterson et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 303 View in Reaxys

NH

NH Cl Cl

O

OH O

Cl

Rx-ID: 261495 View in Reaxys 20/56 Yield

Conditions & References With potassium hydroxide Sanna; ; vol. 4; (1934); p. 28,32 View in Reaxys With sodium hydroxide Whalley; Journal of the Chemical Society; (1954); p. 1651 View in Reaxys With potassium hydroxide Sanna; ; vol. 4; (1934); p. 28,33 View in Reaxys

NH

NH

O O

OH

Cl

O

Rx-ID: 22172979 View in Reaxys 21/56 Yield

Conditions & References Reaction Steps: 2 1: 1,1,2,2-tetrachloro-ethane 2: aqueous NaHCO3 With sodium hydrogencarbonate, tetrachloroethane, 1,1,2,2Peterson et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 303 View in Reaxys

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(v4)

C – (v5) (v5) – (v5) (v5) C(v8) 3+ (v4) Ir N H2 O(v4)

NH

K+

O–

(v2)

C– –O

(v5) (v5) (v4)(v4) (v5) C– Ir3+ (v5) –(v7)

K+ O–

NH

(v3)

O

NH

Rx-ID: 39882992 View in Reaxys 22/56 Yield

Conditions & References

> 99 %Spectr.

in THF-d8 (tetrahydrofuran-d8), Time= 24h, T= 20 °C , Inert atmosphere, Temperature Ueno, Atsushi; Kayaki, Yoshihito; Ikariya, Takao; Organometallics; vol. 33; nb. 17; (2014); p. 4479 - 4485 View in Reaxys

NH

NH

O

OH

H 2N

O

Rx-ID: 118700 View in Reaxys 23/56 Yield

Conditions & References With potassium hydroxide Wegler; Binder; Archiv der Pharmazie (Weinheim, Germany); vol. 275; (1937); p. 506,511 View in Reaxys

NH

NH

N

OH

O

O

Rx-ID: 167146 View in Reaxys 24/56 Yield

Conditions & References With potassium hydroxide Wegler; Binder; Archiv der Pharmazie (Weinheim, Germany); vol. 275; (1937); p. 506,511 View in Reaxys

NH

O

NH

HO OH O

OH O

HN

Rx-ID: 2491152 View in Reaxys 25/56 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, Ambient temperature, Yield given Arai; Masuda; Kiriyama; et al.; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 961 - 969 View in Reaxys

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NH

NH O HO

OH

OH

O

O

HN

Rx-ID: 3174284 View in Reaxys 26/56 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, Ambient temperature Arai; Masuda; Kiriyama; et al.; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 961 - 969 View in Reaxys

NH

O

NH

HO OH O

OH O

HN

Rx-ID: 3207264 View in Reaxys 27/56 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, Ambient temperature Arai; Masuda; Kiriyama; et al.; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 961 - 969 View in Reaxys

NH

NH

OH O

Rx-ID: 72157 View in Reaxys 28/56 Yield

Conditions & References With potassium hydroxide, beim Schmelzen Ciamician; Zatti; Chemische Berichte; vol. 21; (1888); p. 1930; Gazzetta Chimica Italiana; vol. 18; (1888); p. 387 View in Reaxys

NH

NH

OH

OH O

Rx-ID: 104846 View in Reaxys 29/56 Yield

Conditions & References With potassium permanganate, sodium carbonate Mingoia; Gazzetta Chimica Italiana; vol. 62; (1932); p. 844,849 View in Reaxys

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NH

NH

O

OH O

Rx-ID: 106511 View in Reaxys 30/56 Yield

Conditions & References With potassium hydroxide Oddo; Sessa; Gazzetta Chimica Italiana; vol. 41 I; (1911); p. 238 View in Reaxys

O

NH N

N

N

OH O

Rx-ID: 145200 View in Reaxys 31/56 Yield

Conditions & References With acetic acid Sues et al.; Justus Liebigs Annalen der Chemie; vol. 583; (1953); p. 150,155 View in Reaxys

NH

NH O

OH O

Rx-ID: 147271 View in Reaxys 32/56 Yield

Conditions & References With potassium hydroxide Oddo; Gazzetta Chimica Italiana; vol. 43 II; (1913); p. 176 View in Reaxys

NH

NH Cl

O

OH O

Cl

Rx-ID: 157146 View in Reaxys 33/56 Yield

Conditions & References With potassium hydroxide Sanna; ; vol. 4; (1934); p. 28,31 View in Reaxys

HO

OH H 2N 2

NH

N– Br–

O Mg2+

OH O

Rx-ID: 532989 View in Reaxys 34/56 Yield

Conditions & References With diethyl ether, unter Kuehlung mit Eis-Kochsalz-Gemisch Majima; Kotake; Chemische Berichte; vol. 55; (1922); p. 3870; Chemische Berichte; vol. 63; (1930); p. 2239 View in Reaxys With methoxybenzene, unter Kuehlung mit Eis-Kochsalz-Gemisch

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Majima; Kotake; Chemische Berichte; vol. 55; (1922); p. 3870; Chemische Berichte; vol. 63; (1930); p. 2239 View in Reaxys

N NH

O

N

HO OH

OH O

O

OH O

HN

Rx-ID: 3166679 View in Reaxys 35/56 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, Ambient temperature Arai; Masuda; Kiriyama; et al.; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 961 - 969 View in Reaxys

NH

NH O

NH

HO

OH

OH

O

O

OH O

HN

Rx-ID: 3169129 View in Reaxys 36/56 Yield

Conditions & References With sodium hydroxide, dihydrogen peroxide, Ambient temperature Arai; Masuda; Kiriyama; et al.; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 961 - 969 View in Reaxys

O OH HO

OH O

NH

N

indolyl magnesium iodide

H 2N 2

OH O

Rx-ID: 5430458 View in Reaxys 37/56 Yield

Conditions & References With diethyl ether Kasparek; Heacock; Canadian Journal of Chemistry; vol. 45; (1967); p. 771 View in Reaxys

NH

N Cl NH 2 OH

H OH O

Rx-ID: 22197782 View in Reaxys 38/56 Yield

Conditions & References Reaction Steps: 2 1: aqueous HCl; aqueous NaNO2 2: aqueous acetic acid With hydrogenchloride, acetic acid, sodium nitrite

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Sues et al.; Justus Liebigs Annalen der Chemie; vol. 583; (1953); p. 150,155 View in Reaxys

H 2N

H N

O

OH

OH

O

O

NH

NH

N H

O

NH 2

Rx-ID: 32709426 View in Reaxys 39/56 Yield

Conditions & References in methanol, water, Time= 0.166667h, Reflux Smith, Graham; Wermuth, Urs D.; Journal of Chemical Crystallography; vol. 41; nb. 12; (2011); p. 1850 - 1854 View in Reaxys

NH

O

NH NH O

OH

H

NH 2

O

NH OH

HN

N H

O

OH

NH 2

H 2N NH

Rx-ID: 4702765 View in Reaxys 40/56 Yield

Conditions & References With hydrogenchloride, Time= 12h, T= 120 °C , Product distribution Garcia, Angel; Vazquez, Maria Jesus; Quinoa, Emilio; Riguera, Ricardo; Debitus, Cecile; Journal of Natural Products; vol. 59; nb. 8; (1996); p. 782 - 785 View in Reaxys

NH

NH

NH

OH

O

OH

O

Rx-ID: 38868250 View in Reaxys 41/56 Yield

Conditions & References With dihydrogen peroxide, T= 70 °C , Catalytic behavior, Reagent/catalyst, Temperature Rathore, Puran Singh; Thakore, Sonal; Patidar, Rajesh; ; vol. 4; nb. 77; (2014); p. 41111 - 41121 View in Reaxys

NH

NH

H 2N OH

OH O

O

OH

O

O

O

O

NH 2

O

OH

OH

O HO NH 2

O

OH

O

O

OH

NH

NH

HO

O

NH 2 OH

O

N

OH

NH

NH

NH

Rx-ID: 33035256 View in Reaxys 42/56 Yield

Conditions & References Time= 24h, T= 40 °C , pH= 2.6, UV-irradiation, lemon-lime beverage model system

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Upreti, Mani; Somayajula, Kasi V.; Milanowski, Dennis J.; Kowalenko, Peter; Mocek, Ulla; Miguel, Rafael San; Prakash, Indra; Food Chemistry; vol. 131; nb. 2; (2012); p. 413 - 421 View in Reaxys

NH

NH

potassium hydroxide O

OH O

Rx-ID: 5430453 View in Reaxys 43/56 Yield

Conditions & References Zatti; Gazzetta Chimica Italiana; vol. 18; (1888); p. 406; Gazzetta Chimica Italiana; vol. 19; (1889); p. 107 View in Reaxys Zatti; Chemische Berichte; vol. 22; (1889); p. 662; Gazzetta Chimica Italiana; vol. 19; (1889); p. 108 View in Reaxys

NH

NH

O

O

OH O

O

Rx-ID: 345699 View in Reaxys 44/56 Yield

Conditions & References in der Kalischmelze Majima; Shigematsu; Rokkaku; Chemische Berichte; vol. 57; (1924); p. 1455 View in Reaxys

NH NH

O O OH O

HN

Rx-ID: 381860 View in Reaxys 45/56 Yield

Conditions & References bei der Kalischmelze Majima; Shigematsu; Chemische Berichte; vol. 57; (1924); p. 1452 View in Reaxys

NH

NH

S S

S

S OH O

HN

Rx-ID: 456846 View in Reaxys 46/56 Yield

Conditions & References bei der Kalischmelze Oddo; Mingoia; Gazzetta Chimica Italiana; vol. 56; (1926); p. 782 View in Reaxys

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NH

NH

alkaline potassium permanganate solu‐ tion OH

O

O

Rx-ID: 5430448 View in Reaxys 47/56 Yield

Conditions & References Ellinger; Chemische Berichte; vol. 39; (1906); p. 2520 View in Reaxys

NH

NH

KOH-solution OH O

N

Rx-ID: 5430450 View in Reaxys 48/56 Yield

Conditions & References Majima; Shigematsu; Rokkaku; Chemische Berichte; vol. 57; (1924); p. 1455 View in Reaxys

NH

NH

potassium hydroxide OH

O

O

Rx-ID: 5430454 View in Reaxys 49/56 Yield

Conditions & References beim Schmelzen Oddo; Sessa; Gazzetta Chimica Italiana; vol. 41; (1911); p. I 237 View in Reaxys

NH

NH

potassium hydroxide

O

OH O

Rx-ID: 5430455 View in Reaxys 50/56 Yield

Conditions & References beim Schmelzen Oddo; Gazzetta Chimica Italiana; vol. 43; (1913); p. II 198 View in Reaxys

NH

NH H

H O

F

KOH-solution

F O

OH O

F

Rx-ID: 5430451 View in Reaxys 51/56 Yield

Conditions & References Whalley; Journal of the Chemical Society; (1954); p. 1651 View in Reaxys

NH

NH H

H O

Cl

KOH-solution

Cl O

OH O

Cl

Rx-ID: 5430452 View in Reaxys 52/56

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Yield

Conditions & References Sanna; ; vol. 4; (1934); p. 28,33 View in Reaxys

NH

NH

NH

KOH-solution O

O

OH O

O

NH

Rx-ID: 5430456 View in Reaxys 53/56 Yield

Conditions & References Sanna; Gazzetta Chimica Italiana; vol. 52 II; (1922); p. 173 View in Reaxys

NH

NH

NH

NH

O

potassium hydroxide OH

OH O

Rx-ID: 5430457 View in Reaxys 54/56 Yield

Conditions & References beim Schmelzen Ciamician; Zatti; Chemische Berichte; vol. 21; (1888); p. 1930; Gazzetta Chimica Italiana; vol. 18; (1888); p. 387 View in Reaxys Ciamician; Magnanini; Chemische Berichte; vol. 21; (1888); p. 673 View in Reaxys

NH H

OH

H N

O

H

OH O

NH

NH

NH

NH

O

O

NH 2

OH O

OH

HO

O

OH

Rx-ID: 5460162 View in Reaxys 55/56 Yield

Conditions & References Jepson; Biochemical Journal; vol. 69; (1958); p. 22 P View in Reaxys

NH

OH O

Rx-ID: 5430447 View in Reaxys 56/56 Yield

Conditions & References Gilbert,E.E.; Journal of Heterocyclic Chemistry; vol. 6; (1969); p. 483 - 490 View in Reaxys Kasparek; Heacock; Canadian Journal of Chemistry; vol. 45; (1967); p. 771 View in Reaxys Patent; Awramenko et al.; SU444769; (1975); Ref. Zh., Khim.; vol. 14; nb. 0154p; (1976) View in Reaxys Bravo et al.; Tetrahedron Letters; (1969); p. 679 View in Reaxys

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Elkin; Miller; Journal of Pharmaceutical Sciences; vol. 52; (1963); p. 79 View in Reaxys Buechi et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 295; (1962); p.

209,213 View in Reaxys Bravo et al.; Gazzetta Chimica Italiana; vol. 100; (1970); p. 652,656 View in Reaxys Bravo et al.; Tetrahedron Letters; (1970); p. 4535,4536 View in Reaxys Golubey; Suvorov; Khimiya Geterotsiklicheskikh Soedinenii, Sbornik; (1967); p. 21,22-24; ; vol. 70; nb. 77700f; (1969) View in Reaxys Patent; Roussel - UCLAF; GB933566; (1963); ; vol. 60; nb. 2899d; (1964) View in Reaxys Narkevich; Golubev; Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya; vol. 18; (1975); p. 150; ; vol. 82; nb. 170576c; (1975) View in Reaxys Papayan et al.; Armyanskii Khimicheskii Zhurnal; vol. 29; (1976); p. 1062; ; vol. 87; nb. 39217w; (1977) View in Reaxys Katner; Organic Preparations and Procedures; vol. 2; (1970); p. 297,299,301 View in Reaxys Patent; Ruetgersw. Teerverwert.; DE1193946; (1965); ; vol. 63; nb. 13218g; (1965) View in Reaxys Mackie et al.; Journal of Fluorine Chemistry; vol. 10; (1977); p. 437,442 View in Reaxys Mehta et al.; Synthesis; (1978); p. 374 View in Reaxys

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