Issue 34, 2015

Organocatalysed Michael addition on arylmethylidenemalonates involving 4-(2-nitrophenyl)acetoacetate: diversity-oriented access to 8,9-dihydropyrido[1,2-a]indol-6(7H)-one and salicylate scaffolds

Abstract

Excellent diastereoselective (≤96 : 4) preparation of new functionalized 7,8,9-trisubstituted-8,9-dihydropyrido[1,2-a]indol-6(7H)-ones has been achieved in 61–81% yields through a one-pot reductive cycloaromatization–lactamization sequence reaction of Michael adducts using Zn/NH4Cl as a reducing agent. In addition, one-pot synthesis of sterically demanding hexa-substituted salicylate derivatives has been successfully realized via a tandem reaction of alkylidene malonates or aldehydes with 2-nitrophenyl-β-keto ester under aerobic conditions using DBU as an organocatalyst.

Graphical abstract: Organocatalysed Michael addition on arylmethylidenemalonates involving 4-(2-nitrophenyl)acetoacetate: diversity-oriented access to 8,9-dihydropyrido[1,2-a]indol-6(7H)-one and salicylate scaffolds

Supplementary files

Article information

Article type
Communication
Submitted
24 Jan 2015
Accepted
06 Mar 2015
First published
06 Mar 2015

RSC Adv., 2015,5, 26891-26896

Organocatalysed Michael addition on arylmethylidenemalonates involving 4-(2-nitrophenyl)acetoacetate: diversity-oriented access to 8,9-dihydropyrido[1,2-a]indol-6(7H)-one and salicylate scaffolds

A. Srivastava, S. Biswas, S. Singh, S. M. Mobin and S. Samanta, RSC Adv., 2015, 5, 26891 DOI: 10.1039/C5RA01430A

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