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The Barbier‐Type Allylation/Lactamization Cascade Route to Isoindolinones and the Heck‐Type Annulation Route to Isoindolo[2,1‐ a ]quinolines
Author(s) -
Reddy Chennakesava,
Babu Srinivasarao Arulananda,
Padmavathi Rayavarapu
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600411
Subject(s) - annulation , quinoline , intramolecular force , chemistry , combinatorial chemistry , heck reaction , medicinal chemistry , organic chemistry , catalysis , palladium
In this paper, we report the construction of pharmacologically relevant isoindolinones and isoindolo[2,1‐ a ]quinolines through the Zn‐mediated Barbier‐type allylation/lactamization sequential reactions and intramolecular Heck annulation reactions, respectively. The Zn‐mediated Barbier‐type allylation/lactamization sequential reactions of imine systems derived from alkyl 2‐formylbenzoates afforded a library of N ‐substituted 3‐allyl‐isoindolinone scaffolds. Then, this route was applied to assemble various N ‐(2‐haloaryl)‐3‐allyl‐isoindolinone derivatives, which were subsequently subjected to the Pd‐catalyzed intramolecular Heck‐type annulation reaction to afford the corresponding isoindolo[2,1‐ a ]quinoline frameworks. We have shown a formal synthesis of the bio‐active isoindolo[2,1‐ a ]quinoline system 1 g by synthesizing the dione system 12 , which was an intermediate in the Ishihara's scheme pertaining to the synthesis of the bio‐active isoindolo[2,1‐ a ]quinoline system 1 g .