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Access to Substituted Carbazoles in Water by a One‐Pot Sequential Reaction of α,β‐Substituted Nitro Olefins with 2‐(3‐Formyl‐1 H ‐indol‐2‐yl)acetates
Author(s) -
Biswas Soumen,
Dagar Anuradha,
Srivastava Anvita,
Samanta Sampak
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500470
Subject(s) - chemistry , nitro , carbazole , alkyl , imide , one pot synthesis , reaction conditions , combinatorial chemistry , organic chemistry , catalysis , medicinal chemistry
A series of interesting new multifunctional carbazole scaffolds have been prepared in good to excellent yields by an organocatalytic one‐pot two‐step sequential reaction between α‐alkyl‐β‐substituted nitro olefins or α‐alkyl‐δ‐substituted nitro‐dienes and 2‐(3‐formyl‐1 H ‐indol‐2‐yl)acetates in water at room temperature followed by treatment with 2 n HCl under mild conditions. This one‐pot, organocatalytic, oxidant‐free, mild, and eco‐friendly process may provide a powerful alternative synthetic protocol to rapidly access 3‐alkyl‐substituted carbazole frameworks that have a close structural resemblance to biologically active natural carbazoles. Moreover, biologically significant cyclic imide‐ and quinolinone‐fused carbazoles have been efficiently prepared by using this synthetic method.