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Synthesis 2018; 50(24): 4837-4845
DOI: 10.1055/s-0037-1610133
DOI: 10.1055/s-0037-1610133
paper
Sequential Pyridine Dearomatization–Mizoroki–Heck Cyclization for the Construction of Fused (Dihydropyrido)isoindolinone Ring Systems
Early portions of this work were supported by a grant from the U.S. National Science Foundation (CHE-1265488).Further Information
Publication History
Received: 14 February 2018
Accepted after revision: 09 April 2018
Publication Date:
29 May 2018 (online)


Abstract
Acylation of 4-alkylpyridines with 2-iodobenzoyl chlorides under basic conditions results in pyridine dearomatization via formation of 4-alkylidene dihydropyridines. These reasonably stable intermediates are further transformed through Pd-catalyzed Mizoroki–Heck cyclization to afford dihydropyrido-fused isoindolinone products in good yield. This study demonstrates successful harnessing of reactive dearomatized pyridine anhydrobases in metal-catalyzed C–C bond-forming reactions, and provides an efficient entry to isoindolinone ring systems structurally related to several indolizidine alkaloid frameworks.
Key words
dearomatization - Mizoroki–Heck reaction - palladium - isoindolinones - pyridines - alkylidene dihydropyridines - anhydrobasesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610133.
- Supporting Information