8. N–G'zvezdochka', keto beside –N [Reaxys, Reactions (35); 2016-03-23]

Query Query G*

HN

HN

O

1. Query NH

Results

Date

35 reactions in Reaxys

2016-03-23 08h:39m:23s (EST)

G*

NH

Search as: As drawn, No salts, No mixtures

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HN

HN

O

NH

NH

Rx-ID: 9160820 View in Reaxys 1/35 Yield

Conditions & References

87 %

With lithium aluminium tetrahydride in diethyl ether, T= 20 °C Deiters, Alexander; Martin, Stephen F; Organic letters; vol. 4; nb. 19; (2002); p. 3243 - 3245 View in Reaxys With lithium aluminium tetrahydride in diethyl ether, T= 20 °C Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys

N N

N

HN

HN

N

O HN

NH

Rx-ID: 25918201 View in Reaxys 2/35 Yield

Conditions & References

18 %

B1 :Lithium aluminum hydride (423 mg, 0.0011 mol) was added portionwise to a suspension of intermediate 3 (1.0 g, 0.0027 mol) in THF (60 ml) under argon. The mixture was stirred at room temperature for 24 hours, quenched with ice and a diluted Rochelle salt solution, and extracted 3 times with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63 μm) (eluent: DCM/MeOH/NH4OH 95/5/0.1). The pure fractions were collected and the solvent was evaporated, yielding 170 mg (18 percent) of compound 1 as a yellow foam.1H NMR (300 MHz, CDCl3) δ 8.36 (brs, IH), 8.32 (d, 2H, J=6.6), 7.63 (d, IH, J=7.8), 7.39 (d, IH, J=7.5), 7.24-7.11 (m, 3H), 7.07 (d, IH3 J=I.8), 6.93 (d, 2H, J=6.6), 6.58 (s, <n="39"/ >IH), 6.45 (dd, IH, J=8.4, J=2.1), 3.93 (t, 2H} J=8.2), 3.62 (brs, IH), 3.46 (t, 2H, J=7.5),3.09 (m, 4H).LCMS (ES+) m/z 355 (M+l), R1 = 8.30, method A Stage 1: With lithium aluminium tetrahydride in tetrahydrofuran, Time= 24h, T= 20 °C Stage 2: With water, Potassium sodium tartrate in tetrahydrofuran Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/107545; (2007); (A1) English View in Reaxys

N

N

NH

NH

NH

NH

O

Rx-ID: 36112164 View in Reaxys 3/35 Yield 69.3 %

Conditions & References 2 : 4.1.3 General procedure for preparation of compounds 2a–f General procedure: To a solution of compound 1a (0.50 mmol) in 15 mL anhydrous THF, LiAlH4 (1.0 mmol) was added in one portion. The resulting mixture was refluxed for 4 h and carefully quenched with H2O (5.0 mL). The organic layer

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was separated and the aqueous solution was extracted with EtOAc (20 mL×3). The combined organic layer was dried (Na2SO4) and evaporated to dryness to obtain crude product, which was purified by silica gel column chromatography eluting with petroleum, ethyl acetate and triethylamine (20:20:1) to afford 2a.

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 4h, Reflux Tang, Li; Zhao, Liying; Hong, Lingjuan; Yang, Fenyan; Sheng, Rong; Chen, Jianzhong; Shi, Ying; Zhou, Naimin; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 21; nb. 19; (2013); p. 5936 - 5944 View in Reaxys

N

N

NH NH

O

NH NH

Rx-ID: 36112167 View in Reaxys 4/35 Yield

Conditions & References

70.8 %

5 : 4.1.3 General procedure for preparation of compounds 2a–f General procedure: To a solution of compound 1a (0.50 mmol) in 15 mL anhydrous THF, LiAlH4 (1.0 mmol) was added in one portion. The resulting mixture was refluxed for 4 h and carefully quenched with H2O (5.0 mL). The organic layer was separated and the aqueous solution was extracted with EtOAc (20 mL×3). The combined organic layer was dried (Na2SO4) and evaporated to dryness to obtain crude product, which was purified by silica gel column chromatography eluting with petroleum, ethyl acetate and triethylamine (20:20:1) to afford 2a.

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 4h, Reflux Tang, Li; Zhao, Liying; Hong, Lingjuan; Yang, Fenyan; Sheng, Rong; Chen, Jianzhong; Shi, Ying; Zhou, Naimin; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 21; nb. 19; (2013); p. 5936 - 5944 View in Reaxys

N

N HN

HN

N

N

O

NH

NH

Rx-ID: 25918203 View in Reaxys 5/35 Yield 12 %

Conditions & References B2 :Under argon, at room temperature, lithium aluminum hydride (391 mg, 0.010 mol) was added portionwise to a solution of intermediate 6 (1.1 g, 0.0026 mol) in THF (55 ml). The mixture was stirred at room temperature for 18 hours.

The reaction was quenched at 0°C with MeOH. Ice and dilute Rochelle salt solution were added, and the mixture was extracted 3 times with DCM. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63 μm) (eluent: DCM/ MeOH/NH4OH 97/3/0.5). The pure fractions were collected and the solvent was evaporated, yielding 121 mg (12 percent) of compound 2 as an orange foam.1H NMR (300 MHz, CDCl3) δ 8.70 (d, IH, J=5.1), 8.18 (brs, IH), 8.07 (d, IH, J=8.7), 8.03 (d, IH, J=8.7), 7.66 (m, 2H), 7.41 (m, 2H), 7.22 (t, IH, J=7.7), 7.12 (m, 3H)5 6.63 (S3 IH), 6.56 (d, IH, J=8.4), 6.34 (dd, IH, J=8.4, J=2.1), 4.06 (t, 2H, J=7.8), 3.46 (t, 2H, J=6.8), 3.12 (m, 4H). MS (ES+) m/z 405 (M+l).

Stage 1: With lithium aluminium tetrahydride in tetrahydrofuran, Time= 18h, T= 20 °C Stage 2: With methanol in tetrahydrofuran, T= 0 °C Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/107545; (2007); (A1) English View in Reaxys

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N

N

NH

NH

O

NH

N H

Rx-ID: 36112165 View in Reaxys 6/35 Yield

Conditions & References

63.2 %

3 : 4.1.3 General procedure for preparation of compounds 2a–f General procedure: To a solution of compound 1a (0.50 mmol) in 15 mL anhydrous THF, LiAlH4 (1.0 mmol) was added in one portion. The resulting mixture was refluxed for 4 h and carefully quenched with H2O (5.0 mL). The organic layer was separated and the aqueous solution was extracted with EtOAc (20 mL×3). The combined organic layer was dried (Na2SO4) and evaporated to dryness to obtain crude product, which was purified by silica gel column chromatography eluting with petroleum, ethyl acetate and triethylamine (20:20:1) to afford 2a.

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 4h, Reflux Tang, Li; Zhao, Liying; Hong, Lingjuan; Yang, Fenyan; Sheng, Rong; Chen, Jianzhong; Shi, Ying; Zhou, Naimin; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 21; nb. 19; (2013); p. 5936 - 5944 View in Reaxys

O

N

O

N

NH

NH

NH

NH

O

Rx-ID: 36112166 View in Reaxys 7/35 Yield

Conditions & References

59.8 %

4 : 4.1.3 General procedure for preparation of compounds 2a–f General procedure: To a solution of compound 1a (0.50 mmol) in 15 mL anhydrous THF, LiAlH4 (1.0 mmol) was added in one portion. The resulting mixture was refluxed for 4 h and carefully quenched with H2O (5.0 mL). The organic layer was separated and the aqueous solution was extracted with EtOAc (20 mL×3). The combined organic layer was dried (Na2SO4) and evaporated to dryness to obtain crude product, which was purified by silica gel column chromatography eluting with petroleum, ethyl acetate and triethylamine (20:20:1) to afford 2a.

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 4h, Reflux Tang, Li; Zhao, Liying; Hong, Lingjuan; Yang, Fenyan; Sheng, Rong; Chen, Jianzhong; Shi, Ying; Zhou, Naimin; Hu, Yongzhou; Bioorganic and Medicinal Chemistry; vol. 21; nb. 19; (2013); p. 5936 - 5944 View in Reaxys

N

N

HN

HN

N

N

O

NH

NH

Rx-ID: 25918208 View in Reaxys 8/35 Yield

Conditions & References B6 :Intermediate 16 (0.001 mol) was added portionwise to a solution of lithium aluminum tetrahydride (0..002 mol) in THF (10ml) under N2 flow. The mixture was stirred and refluxed for 24 hours, poured out into ice water and filtered over

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celite. Celite was washed with EtOAc. The filtrate was extracted with EtOAc. The organic layer was <n="42"/>separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (0.45g) was purified by column chromatography over silica gel (lOμm) (eluent:DCM/MeOH/NH4OH 95/5/0.5). The pure fractions were collected and the solvent was evaporated, yielding 0.042 g of compound 6.1H NMR (DMSO-d6) δ 1.28(6H,s), 2.95(2H,t,J=7.7Hz), 3.27-3.34(2H,m), 3.65(2H,s),5.38(lH,br,t,J=6.4Hz), 6.45(lH,dd,J=4Hz ,7.7Hz), 6.57(lH,d,J=4Hz), 6.96-7.02(3H5In),7.07(lH,t,J=7.7Hz), 7.15-7.5(3H,m)J7.35(lH,d,J=7.7Hz), 7.55(lH,d,J=7.7Hz),8.22(lH,d,J=7.7Hz), 10.83(lH,br,s)MS (ES+) m/z 383 (M+l), R1 = 9.17, method A Stage 1: With lithium aluminium tetrahydride in tetrahydrofuran, Time= 24h, Heating / reflux Stage 2: With water in tetrahydrofuran Patent; JANSSEN PHARMACEUTICA N.V.; WO2007/107545; (2007); (A1) English View in Reaxys

O

Si O

O

O

O

O Si

HN

HN

O HN NH

Rx-ID: 3164346 View in Reaxys 9/35 Yield

Conditions & References

95 %

With diisobutylaluminium hydride in tetrahydrofuran, toluene, Time= 4h, Heating Trost, Barry M.; Romero, Arthur G.; Journal of Organic Chemistry; vol. 51; nb. 12; (1986); p. 2332 - 2342 View in Reaxys

O

HO

HO O HN

Br

HN

Br

O N H

NH

Rx-ID: 8976697 View in Reaxys 10/35 Yield

Conditions & References

62 %

Stage 1: With dimethylsulfide borane complex in tetrahydrofuran, Time= 0.333333h, Heating Stage 2: in methanol, Time= 0.0333333h, T= 20 °C Stage 3: With hydrogenchloride, water, Time= 0.5h, T= 0 °C Lawrence, Nicholas; Bushell, Simon; Tetrahedron Letters; vol. 42; nb. 43; (2001); p. 7671 - 7674 View in Reaxys F

F

NH N HN

NH N

Cl

N

Cl

N

HN

Cl

N N

O HN

HN

Rx-ID: 25037313 View in Reaxys 11/35

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Yield

Conditions & References 60 : EXAMPLE 60 EXAMPLE 60 To a stirred mixture of 0.8 parts of lithium aluminum hydride and 135 parts of tetrahydrofuran were added slowly 4 parts of N-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]amino]-1-piperidinyl]ethyl]-1H-indol-3-acetamide.

The whole was stirred and refluxed overnight.

The reaction mixture was cooled in an ice bath and decomposed by the successive additions of 1 part of water, 4.5 parts of a sodium hydroxide solution 15percent and 3 parts of water.

The whole was filtered over Hyflo and the filtrate was evaporated.

The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (96:4 by volume) saturated with ammonia, as eluent.

The pure fractions were collected and the eluent was evaporated.

The residue was crystallized from acetonitrile, yielding 1 part (25.5percent) of 1-[(4-fluorophenyl)methyl]-N-[1-[2-[[2(1H-indol-3-yl)ethyl]amino]ethyl]-4-piperidinyl]-1H-benzimidazol-2-amine; mp. 169.7° C. (compound 107).

With sodium hydroxide in tetrahydrofuran, methanol, water Patent; Janssen Pharmaceutica, N.V.; US4634704; (1987); (A1) English View in Reaxys

O

O O

O O

O O

O

HN

HN O

NH

NH

Rx-ID: 9168299 View in Reaxys 12/35 Yield

Conditions & References

86 %

With lithium aluminium tetrahydride in 1,4-dioxane, Heating Miyazawa, Norio; Ogasawara, Kunio; Tetrahedron Letters; vol. 43; nb. 27; (2002); p. 4773 - 4776 View in Reaxys

N

N

HN

HN

O

NH

NH

Rx-ID: 5150863 View in Reaxys 13/35 Yield

Conditions & References

90 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, Heating Fouchard, Fabienne; Menciu, Cecilia; Duflos, Muriel; Baut, Guillaume Le; Lambrey, Bernard; Mourgues, Marie; Perrissoud, Daniel; Arzneimittel-Forschung/Drug Research; vol. 49; nb. 2; (1999); p. 96 - 105 View in Reaxys N

N

HN

HN

O

NH

NH

Rx-ID: 5155933 View in Reaxys 14/35

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Yield

Conditions & References

85 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, Heating Fouchard, Fabienne; Menciu, Cecilia; Duflos, Muriel; Baut, Guillaume Le; Lambrey, Bernard; Mourgues, Marie; Perrissoud, Daniel; Arzneimittel-Forschung/Drug Research; vol. 49; nb. 2; (1999); p. 96 - 105 View in Reaxys

O HN

HN NH

NH

Rx-ID: 38762547 View in Reaxys 15/35 Yield

Conditions & References

88 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 16h, Reflux, Inert atmosphere Chiou, Wen-Hua; Wang, Yu-Wei; Kao, Chien-Lun; Chen, Po-Chou; Wu, Chen-Chang; Organometallics; vol. 33; nb. 16; (2014); p. 4240 - 4244 View in Reaxys

HN

HN

O

NH

NH

Rx-ID: 3614452 View in Reaxys 16/35 Yield

Conditions & References

72 %

With lithium aluminium tetrahydride in diethyl ether, Time= 16h, Heating Darbre, Tamis; Nussbaumer, Cornelius; Borschberg, Hans-Juerg; Helvetica Chimica Acta; vol. 67; (1984); p. 1040 - 1052 View in Reaxys

NH

N

NH

NH

OH

HN

N

HN O

O

O HN HN

HN

NH

Rx-ID: 9379837 View in Reaxys 17/35 Yield 52 %, 8 %

Conditions & References With formic acid in water, Time= 3h, T= 20 °C Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys

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N

N

HN

HN

O

NH

NH

Rx-ID: 5167664 View in Reaxys 18/35 Yield

Conditions & References

72 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, Heating Fouchard, Fabienne; Menciu, Cecilia; Duflos, Muriel; Baut, Guillaume Le; Lambrey, Bernard; Mourgues, Marie; Perrissoud, Daniel; Arzneimittel-Forschung/Drug Research; vol. 49; nb. 2; (1999); p. 96 - 105 View in Reaxys

N

N

HN

HN

O

NH

NH

Rx-ID: 5169856 View in Reaxys 19/35 Yield

Conditions & References

70 %

With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, Heating Fouchard, Fabienne; Menciu, Cecilia; Duflos, Muriel; Baut, Guillaume Le; Lambrey, Bernard; Mourgues, Marie; Perrissoud, Daniel; Arzneimittel-Forschung/Drug Research; vol. 49; nb. 2; (1999); p. 96 - 105 View in Reaxys

HO

HO

HN

HN O

NH

NH

Rx-ID: 9427612 View in Reaxys 20/35 Yield

Conditions & References

58 %

With lithium aluminium tetrahydride in tetrahydrofuran, diethyl ether, Time= 18h, Heating Decker, Michael; Lehmann, Jochen; Archiv der Pharmazie; vol. 336; nb. 10; (2003); p. 466 - 476 View in Reaxys

HO

HO

HN

HN O

NH

NH

Rx-ID: 8973840 View in Reaxys 21/35 Yield 45 %

Conditions & References With lithium aluminium tetrahydride in diethyl ether, Time= 18h, Heating Decker, Michael; Faust, Ruediger; Wedig, Maike; Nieger, Martin; Holzgrabe, Ulrike; Lehmann, Jochen; Heterocycles; vol. 55; nb. 8; (2001); p. 1455 - 1466 View in Reaxys

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NH

NH

NH

NH HN

O

HN

O

O

O

HN

HN

NH

HN

NH

NH

Rx-ID: 9412212 View in Reaxys 22/35 Yield

Conditions & References

13 %, 27 %, 9 %

With sodium cyanoborohydride in acetic acid, Time= 3h, T= 20 °C Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys

OH

O

Si HN

HN O NH

NH

Rx-ID: 3710773 View in Reaxys 23/35 Yield

Conditions & References With sodium bis(2-methoxyethoxy)aluminium dihydride in toluene, Time= 10h, Heating Ihara, Masataka; Setsu, Fumihito; Shohda, Miyuki; Taniguchi, Nobuaki; Tokunaga, Yuji; Fukumoto, Keiichiro; Journal of Organic Chemistry; vol. 59; nb. 18; (1994); p. 5317 - 5323 View in Reaxys

O

Si

O

HN

Si

HN O

NH

NH

Rx-ID: 18367767 View in Reaxys 24/35 Yield

Conditions & References Reaction Steps: 2 1: NaAl(OCH2CH2OMe)2H2 / toluene / 10 h / Heating 2: DMAP, Et3N / CH2Cl2 / 9.5 h / Ambient temperature With 4-(N,N-dimethlyamino)pyridine, triethylamine, sodium bis(2-methoxyethoxy)aluminium dihydride in dichloromethane, toluene Ihara, Masataka; Setsu, Fumihito; Shohda, Miyuki; Taniguchi, Nobuaki; Tokunaga, Yuji; Fukumoto, Keiichiro; Journal of Organic Chemistry; vol. 59; nb. 18; (1994); p. 5317 - 5323 View in Reaxys

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S

S S

S O

OH

HN

HN OH O

NH

NH

Rx-ID: 4195110 View in Reaxys 25/35 Yield

Conditions & References With lithium aluminium tetrahydride in 1,4-dioxane, Heating, Yield given Kawamura; Ogasawara; Tetrahedron Letters; vol. 36; nb. 19; (1995); p. 3369 - 3372 View in Reaxys S

S

N

N O

HN

HN O

NH

NH

Rx-ID: 9223309 View in Reaxys 26/35 Yield

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Heating Altamura, Maria; Canfarini, Franca; Catalioto, Rose-Marie; Guidi, Antonio; Pasqui, Franco; Renzetti, Anna R.; Triolo, Antonio; Maggi, Carlo A.; Bioorganic and Medicinal Chemistry Letters; vol. 12; nb. 20; (2002); p. 2945 - 2948 View in Reaxys

NH

N HN

HN O

O

NH

NH

HN

Rx-ID: 14176361 View in Reaxys 27/35 Yield

Conditions & References Reaction Steps: 3 1: 9 percent / NaBH3CN / acetic acid / 3 h / 20 °C 2: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 3: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With sodium tungstate, formic acid, dihydrogen peroxide, sodium cyanoborohydride in methanol, water, acetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys Reaction Steps: 3 1: 90 percent / Et3SiH / trifluoroacetic acid / 4 h / 65 - 75 °C 2: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 3: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With triethylsilane, sodium tungstate, formic acid, dihydrogen peroxide in methanol, water, trifluoroacetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600

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View in Reaxys Reaction Steps: 3 1: 42 percent / NaBH3CN / trifluoroacetic acid; acetic acid / 1.5 h / 20 °C 2: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 3: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With sodium tungstate, formic acid, dihydrogen peroxide, sodium cyanoborohydride in methanol, water, acetic acid, trifluoroacetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys

N

N

OH

HN

HN O

NH

O HN

HN

Rx-ID: 14182455 View in Reaxys 28/35 Yield

Conditions & References Reaction Steps: 4 1: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C 2: 9 percent / NaBH3CN / acetic acid / 3 h / 20 °C 3: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 4: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With sodium tungstate, formic acid, dihydrogen peroxide, sodium cyanoborohydride in methanol, water, acetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys Reaction Steps: 4 1: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C 2: 90 percent / Et3SiH / trifluoroacetic acid / 4 h / 65 - 75 °C 3: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 4: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With triethylsilane, sodium tungstate, formic acid, dihydrogen peroxide in methanol, water, trifluoroacetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys Reaction Steps: 4 1: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C 2: 42 percent / NaBH3CN / trifluoroacetic acid; acetic acid / 1.5 h / 20 °C 3: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 4: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With sodium tungstate, formic acid, dihydrogen peroxide, sodium cyanoborohydride in methanol, water, acetic acid, trifluoroacetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys

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NH N

HN HN O

O

NH

NH

HN

Rx-ID: 14202050 View in Reaxys 29/35 Yield

Conditions & References Reaction Steps: 5 1: 55 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.25 h / 20 °C 2: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C 3: 9 percent / NaBH3CN / acetic acid / 3 h / 20 °C 4: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 5: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With sodium tungstate, formic acid, dihydrogen peroxide, sodium cyanoborohydride in methanol, water, acetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys Reaction Steps: 5 1: 55 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.25 h / 20 °C 2: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C 3: 90 percent / Et3SiH / trifluoroacetic acid / 4 h / 65 - 75 °C 4: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 5: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With triethylsilane, sodium tungstate, formic acid, dihydrogen peroxide in methanol, water, trifluoroacetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys Reaction Steps: 5 1: 55 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.25 h / 20 °C 2: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C 3: 42 percent / NaBH3CN / trifluoroacetic acid; acetic acid / 1.5 h / 20 °C 4: 51 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.17 h / 20 °C 5: 3 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With sodium tungstate, formic acid, dihydrogen peroxide, sodium cyanoborohydride in methanol, water, acetic acid, trifluoroacetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys

N

N

HN

HN S

S

O

NH

NH

Rx-ID: 922045 View in Reaxys 30/35 Yield

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 4h, Heating Biniecki,S.; Horoszkiewicz,Z.; Roczniki Chemii; vol. 48; (1974); p. 857 - 859 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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N HN

N HN

S

S

O

NH

NH

Rx-ID: 922901 View in Reaxys 31/35 Yield

Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 6h, Heating Biniecki,S.; Horoszkiewicz,Z.; Roczniki Chemii; vol. 48; (1974); p. 857 - 859 View in Reaxys

N

NH

OH

HN

HN O

O HN

HN

Rx-ID: 14182451 View in Reaxys 32/35 Yield

Conditions & References Reaction Steps: 2 1: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C 2: 13 percent / NaBH3CN / acetic acid / 3 h / 20 °C With formic acid, sodium cyanoborohydride in water, acetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys

NH NH

HN HN O

O

NH

HN

Rx-ID: 14202044 View in Reaxys 33/35 Yield

Conditions & References Reaction Steps: 2 1: 55 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.25 h / 20 °C 2: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C With sodium tungstate, formic acid, dihydrogen peroxide in methanol, water Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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NH NH

HN HN O

O

NH

HN

Rx-ID: 14202046 View in Reaxys 34/35 Yield

Conditions & References Reaction Steps: 3 1: 55 percent / Na2WO4*2H2O; 30 percent H2O2 / methanol; H2O / 0.25 h / 20 °C 2: 8 percent / 85 percent HCOOH / H2O / 3 h / 20 °C 3: 13 percent / NaBH3CN / acetic acid / 3 h / 20 °C With sodium tungstate, formic acid, dihydrogen peroxide, sodium cyanoborohydride in methanol, water, acetic acid Nakai, Yu-ya; Goto, Aya; Yamada, Fumio; Somei, Masanori; Heterocycles; vol. 60; nb. 7; (2003); p. 1589 - 1600 View in Reaxys

HN

HN

O

N H

NH

Rx-ID: 335382 View in Reaxys 35/35 Yield

Conditions & References With lithium aluminium tetrahydride Katritzky; Journal of the Chemical Society; (1955); p. 2586,2591 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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