e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Direct acylamination of pyridine 1-oxide with N-phenylarenimidoyl chlorides and fluorides

RA Abramovitch, J Pilski, A Konitz…

Index: Abramovitch, Rudolph A.; Pilski, Jacek; Konitz, Antoni; Tomasik, Piotr Journal of Organic Chemistry, 1983 , vol. 48, # 23 p. 4391 - 4393

Full Text: HTML

Citation Number: 11

Abstract

Pyridine 1-oxide reacts with N-phenylbenzimidoyl chloride to give 2-(N-benzoylanilino) pyridine (2) and 3-chloropyridine (I).'When substituted N-phenylbenzimidoyl chlorides are used, the yields of acylaminated pyridine and of 1 depend on the substituents present in both the anilide'and the acyl2 moieties of the imidoyl chloride. Preliminary results2 of the reaction of pyridine 1-oxide with some N-phenylarenimidoyl chlorides suggested that ...

Natrium-[4-(1,1,3,3-tetramethyl-butyl)-phenolat] Structure

Natrium-[4-(1,1...

~43%

3-Chloropyridine Structure

3-Chloropyridine

2-methoxy-N-phenylbenzamide Structure

2-methoxy-N-phe...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

Natrium-[4-(1,1,3,3-tetramethyl-butyl)-phenolat] Structure

Natrium-[4-(1,1...

~42%

3-Chloropyridine Structure

3-Chloropyridine

2-methoxy-N-phenylbenzamide Structure

2-methoxy-N-phe...

Detail Learn More

N-Phenyl-o-nitrobenzimidoyl chloride Structure

N-Phenyl-o-nitr...

~64%

3-Chloropyridine Structure

3-Chloropyridine

2-NITROBENZANILIDE Structure

2-NITROBENZANILIDE

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

N-Phenyl-o-nitrobenzimidoyl chloride Structure

N-Phenyl-o-nitr...

~66%

3-Chloropyridine Structure

3-Chloropyridine

2-NITROBENZANILIDE Structure

2-NITROBENZANILIDE

Detail Learn More

3,5-dinitro-N-phenylbenzimidoyl chloride Structure

3,5-dinitro-N-p...

~88%

3-Chloropyridine Structure

3-Chloropyridine

3,5-dinitro-N-phenyl-benzamide Structure

3,5-dinitro-N-p...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Learn More

2-Chlor-N-phenylbenzimidchlorid Structure

2-Chlor-N-pheny...

~49%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,2-chloro-N-phenyl Structure

Benzamide,2-chl...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

2-Chlor-N-phenylbenzimidchlorid Structure

2-Chlor-N-pheny...

~48%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,2-chloro-N-phenyl Structure

Benzamide,2-chl...

Detail Learn More

N-phenyl-m-chlorobenzimidoyl chloride Structure

N-phenyl-m-chlo...

~50%

3-Chloropyridine Structure

3-Chloropyridine

3-chloro-N-phenylbenzamide Structure

3-chloro-N-phen...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

N-phenyl-m-chlorobenzimidoyl chloride Structure

N-phenyl-m-chlo...

~49%

3-Chloropyridine Structure

3-Chloropyridine

3-chloro-N-phenylbenzamide Structure

3-chloro-N-phen...

Detail Learn More

3-methyl-N-phenyl-benzimidoyl chloride Structure

3-methyl-N-phen...

~46%

3-Chloropyridine Structure

3-Chloropyridine

3-METHYLBENZANILIDE Structure

3-METHYLBENZANILIDE

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

3-methyl-N-phenyl-benzimidoyl chloride Structure

3-methyl-N-phen...

~47%

3-Chloropyridine Structure

3-Chloropyridine

3-METHYLBENZANILIDE Structure

3-METHYLBENZANILIDE

Detail Learn More

2,4-dichloro-N-phenylbenzimidoyl chloride Structure

2,4-dichloro-N-...

~54%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,2,4-dichloro-N-phenyl Structure

Benzamide,2,4-d...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

2,4-dichloro-N-phenylbenzimidoyl chloride Structure

2,4-dichloro-N-...

~55%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,2,4-dichloro-N-phenyl Structure

Benzamide,2,4-d...

Detail Learn More

pyridine oxide Structure

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,3-nitro-N-phenyl Structure

Benzamide,3-nit...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

3-nitro-N-phenyl-benzimidoyl chloride Structure

3-nitro-N-pheny...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,3-nitro-N-phenyl Structure

Benzamide,3-nit...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

N-phenyl-m-chlorobenzimidoyl chloride Structure

N-phenyl-m-chlo...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3-chloro-N-phenylbenzamide Structure

3-chloro-N-phen...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

2-Chlor-N-phenylbenzimidchlorid Structure

2-Chlor-N-pheny...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,2-chloro-N-phenyl Structure

Benzamide,2-chl...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

N-Phenyl-o-nitrobenzimidoyl chloride Structure

N-Phenyl-o-nitr...

~0%

3-Chloropyridine Structure

3-Chloropyridine

2-NITROBENZANILIDE Structure

2-NITROBENZANILIDE

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

3-methoxy-N-phenylbenzimidoyl chloride Structure

3-methoxy-N-phe...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3-Methoxy-N-phenylbenzamide Structure

3-Methoxy-N-phe...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

2,4-dichloro-N-phenylbenzimidoyl chloride Structure

2,4-dichloro-N-...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,2,4-dichloro-N-phenyl Structure

Benzamide,2,4-d...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

3,5-dimethoxy-N-phenylbenzimidoyl chloride Structure

3,5-dimethoxy-N...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3,5-dimethoxy-N-phenylbenzamide Structure

3,5-dimethoxy-N...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

2,4-dinitro-N-phenylbenzimidoyl chloride Structure

2,4-dinitro-N-p...

~0%

3-Chloropyridine Structure

3-Chloropyridine

2,4-Dinitrobenzanilide Structure

2,4-Dinitrobenz...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Learn More

2-methyl-N-phenyl-benzimidoyl chloride Structure

2-methyl-N-phen...

~0%

3-Chloropyridine Structure

3-Chloropyridine

2-METHYL-N-PHENYLBENZAMIDE Structure

2-METHYL-N-PHEN...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

3-methyl-N-phenyl-benzimidoyl chloride Structure

3-methyl-N-phen...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3-METHYLBENZANILIDE Structure

3-METHYLBENZANILIDE

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

3,5-dimethyl-N-phenylbenzimidoyl chloride Structure

3,5-dimethyl-N-...

~0%

3-Chloropyridine Structure

3-Chloropyridine

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

3,5-dimethyl-N-phenylbenzamide Structure

3,5-dimethyl-N-...

Detail Learn More

3,4-dichloro-N-phenylbenzimidoyl chloride Structure

3,4-dichloro-N-...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3,4-Dichlorobenzanilide Structure

3,4-Dichloroben...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

Natrium-[4-(1,1,3,3-tetramethyl-butyl)-phenolat] Structure

Natrium-[4-(1,1...

~0%

3-Chloropyridine Structure

3-Chloropyridine

2-methoxy-N-phenylbenzamide Structure

2-methoxy-N-phe...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

3,5-dinitro-N-phenylbenzimidoyl chloride Structure

3,5-dinitro-N-p...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3,5-dinitro-N-phenyl-benzamide Structure

3,5-dinitro-N-p...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Learn More

2,4-dimethyl-N-phenylbenzimidoyl chloride Structure

2,4-dimethyl-N-...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide, 2,4-dimethyl-N-phenyl Structure

Benzamide, 2,4-...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

N-Phenyl-2,4-dimethoxybenzimidoyl chloride Structure

N-Phenyl-2,4-di...

~0%

3-Chloropyridine Structure

3-Chloropyridine

N/A Structure

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

3-nitro-N-phenyl-benzimidoyl chloride Structure

3-nitro-N-pheny...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,3-nitro-N-phenyl Structure

Benzamide,3-nit...

Detail Learn More

pyridine oxide Structure

N-phenyl-m-chlorobenzimidoyl chloride Structure

N-phenyl-m-chlo...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3-chloro-N-phenylbenzamide Structure

3-chloro-N-phen...

Detail Learn More

pyridine oxide Structure

2-Chlor-N-phenylbenzimidchlorid Structure

2-Chlor-N-pheny...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,2-chloro-N-phenyl Structure

Benzamide,2-chl...

Detail Learn More

pyridine oxide Structure

N-Phenyl-o-nitrobenzimidoyl chloride Structure

N-Phenyl-o-nitr...

~0%

3-Chloropyridine Structure

3-Chloropyridine

2-NITROBENZANILIDE Structure

2-NITROBENZANILIDE

Detail Learn More

pyridine oxide Structure

3-methoxy-N-phenylbenzimidoyl chloride Structure

3-methoxy-N-phe...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3-Methoxy-N-phenylbenzamide Structure

3-Methoxy-N-phe...

Detail Learn More

pyridine oxide Structure

2,4-dichloro-N-phenylbenzimidoyl chloride Structure

2,4-dichloro-N-...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,2,4-dichloro-N-phenyl Structure

Benzamide,2,4-d...

Detail Learn More

pyridine oxide Structure

3,5-dimethoxy-N-phenylbenzimidoyl chloride Structure

3,5-dimethoxy-N...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3,5-dimethoxy-N-phenylbenzamide Structure

3,5-dimethoxy-N...

Detail Learn More

pyridine oxide Structure

2-methyl-N-phenyl-benzimidoyl chloride Structure

2-methyl-N-phen...

~0%

3-Chloropyridine Structure

3-Chloropyridine

2-METHYL-N-PHENYLBENZAMIDE Structure

2-METHYL-N-PHEN...

Detail Learn More

pyridine oxide Structure

3-methyl-N-phenyl-benzimidoyl chloride Structure

3-methyl-N-phen...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3-METHYLBENZANILIDE Structure

3-METHYLBENZANILIDE

Detail Learn More

pyridine oxide Structure

3,5-dimethyl-N-phenylbenzimidoyl chloride Structure

3,5-dimethyl-N-...

~0%

3-Chloropyridine Structure

3-Chloropyridine

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

3,4-dichloro-N-phenylbenzimidoyl chloride Structure

3,4-dichloro-N-...

~0%

3-Chloropyridine Structure

3-Chloropyridine

3,4-Dichlorobenzanilide Structure

3,4-Dichloroben...

Detail Learn More

pyridine oxide Structure

Natrium-[4-(1,1,3,3-tetramethyl-butyl)-phenolat] Structure

Natrium-[4-(1,1...

~0%

3-Chloropyridine Structure

3-Chloropyridine

2-methoxy-N-phenylbenzamide Structure

2-methoxy-N-phe...

Detail Learn More

pyridine oxide Structure

2,4-dimethyl-N-phenylbenzimidoyl chloride Structure

2,4-dimethyl-N-...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide, 2,4-dimethyl-N-phenyl Structure

Benzamide, 2,4-...

Detail Learn More

pyridine oxide Structure

N-Phenyl-2,4-dimethoxybenzimidoyl chloride Structure

N-Phenyl-2,4-di...

~0%

3-Chloropyridine Structure

3-Chloropyridine

N/A Structure

Detail Learn More

pyridine oxide Structure

1-chloro-N,1-diphenyl-methanimine Structure

1-chloro-N,1-di...

~0%

3-Chloropyridine Structure

3-Chloropyridine

Benzanilide Structure

Detail Learn More

pyridine oxide Structure

~61%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,3-nitro-N-phenyl Structure

Benzamide,3-nit...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

3-nitro-N-phenyl-benzimidoyl chloride Structure

3-nitro-N-pheny...

~63%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,3-nitro-N-phenyl Structure

Benzamide,3-nit...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

3-nitro-N-phenyl-benzimidoyl chloride Structure

3-nitro-N-pheny...

~64%

3-Chloropyridine Structure

3-Chloropyridine

Benzamide,3-nitro-N-phenyl Structure

Benzamide,3-nit...

Detail Learn More

2-methyl-N-phenyl-benzimidoyl chloride Structure

2-methyl-N-phen...

~38%

3-Chloropyridine Structure

3-Chloropyridine

2-METHYL-N-PHENYLBENZAMIDE Structure

2-METHYL-N-PHEN...

1-oxidopyridin-1-ium,hydrochloride Structure

1-oxidopyridin-...

Detail Learn More

pyridine oxide Structure

2-methyl-N-phenyl-benzimidoyl chloride Structure

2-methyl-N-phen...

~39%

3-Chloropyridine Structure

3-Chloropyridine

2-METHYL-N-PHENYLBENZAMIDE Structure

2-METHYL-N-PHEN...

Detail Learn More

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Synthesis of amides through the Cannizzaro-type reaction cat...

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