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

Tetrahedron

Sodium borohydride–iodine mediated reduction of γ-lactam carboxylic acids followed by DDQ mediated oxidative aromatisation: a simple approach towards N-aryl- …

P Haldar, G Barman, JK Ray

Index: Haldar, Pranab; Barman, Gopa; Ray, Jayanta K. Tetrahedron, 2007 , vol. 63, # 14 p. 3049 - 3056

Full Text: HTML

Citation Number: 21

Abstract

A simple methodology for the conversion of substituted N-aryl-γ-lactam 2/3-carboxylic acids to substituted N-aryl-2/3-formyl-pyrroles has been developed. Several N-aryl-γ-lactam 2/3- carboxylic acids were reduced to substituted (N-aryl-pyrroliden-2/3-yl)-methanols in good yields by using the NaBH4–I2 system. Aromatisation and in situ oxidation of these alcohols using DDQ produced N-aryl-2/3-formyl-pyrroles, which act as key starting material and ...

6,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione Structure

6,6-Dimethyl-5,...

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

~83%

1-(3,4-dichlorophenyl)-2-oxopyrrolidine-3-carboxylic acid Structure

1-(3,4-dichloro...

6,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione Structure

6,6-Dimethyl-5,...

4-Bromoaniline Structure

~73%

3-PYRROLIDINECARBOXYLIC ACID, 1-(4-BROMOPHENYL)-2-OXO- Structure

3-PYRROLIDINECA...

6,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione Structure

6,6-Dimethyl-5,...

p-Toluidine Structure

~81%

3-PYRROLIDINECARBOXYLIC ACID, 1-(4-METHYLPHENYL)-2-OXO- Structure

3-PYRROLIDINECA...

6,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione Structure

6,6-Dimethyl-5,...

4-Chloroaniline Structure

4-Chloroaniline

~82%

3-PYRROLIDINECARBOXYLIC ACID, 1-(4-CHLOROPHENYL)-2-OXO- Structure

3-PYRROLIDINECA...

[1-(4-bromophenyl)pyrrolidin-3-yl]methanol Structure

[1-(4-bromophen...

~65%

1-(4-bromophenyl)pyrrole-3-carbaldehyde Structure

1-(4-bromopheny...

3-PYRROLIDINECARBOXYLIC ACID, 1-(4-BROMOPHENYL)-2-OXO- Structure

3-PYRROLIDINECA...

~%

1-(4-bromophenyl)pyrrole-3-carbaldehyde Structure

1-(4-bromopheny...

4-Bromoaniline Structure

~%

1-(4-bromophenyl)pyrrole-3-carbaldehyde Structure

1-(4-bromopheny...

Itaconic acid Structure

~%

1-(4-bromophenyl)pyrrole-3-carbaldehyde Structure

1-(4-bromopheny...

1-(4-BROMO-PHENYL)-3,3-BIS-METHYLSULFANYL-PROPENONE Structure

1-(4-BROMO-PHEN...

~%

1-(4-bromophenyl)pyrrole-3-carbaldehyde Structure

1-(4-bromopheny...

Itaconic acid Structure

3,4-Dichloroaniline Structure

3,4-Dichloroaniline

~91%

1-(3,4-DICHLOROPHENYL)-5-OXO-3-PYRROLIDINECARBOXYLIC ACID Structure

1-(3,4-DICHLORO...

6,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione Structure

6,6-Dimethyl-5,...

3-Chloro-4-fluoroaniline Structure

3-Chloro-4-fluo...

~77%

1-(3-chloro-4-fluorophenyl)-2-oxopyrrolidine-3-carboxylic acid Structure

1-(3-chloro-4-f...

1-(4-chlorophenyl)-3-hydroxymethylpyrrolidine Structure

1-(4-chlorophen...

~66%

1-(4-chlorophenyl)pyrrole-3-carbaldehyde Structure

1-(4-chlorophen...

3-PYRROLIDINECARBOXYLIC ACID, 1-(4-CHLOROPHENYL)-2-OXO- Structure

3-PYRROLIDINECA...

~%

1-(4-chlorophenyl)pyrrole-3-carbaldehyde Structure

1-(4-chlorophen...

4-Chloroaniline Structure

4-Chloroaniline

~%

1-(4-chlorophenyl)pyrrole-3-carbaldehyde Structure

1-(4-chlorophen...

Itaconic acid Structure

~%

1-(4-chlorophenyl)pyrrole-3-carbaldehyde Structure

1-(4-chlorophen...

1-(4-chloro-phenyl)-5-oxo-pyrrolidine-3-carboxylic acid Structure

1-(4-chloro-phe...

~%

1-(4-chlorophenyl)pyrrole-3-carbaldehyde Structure

1-(4-chlorophen...