Journal article
Sequential Pyridine Dearomatization–Mizoroki–Heck Cyclization for the Construction of Fused (Dihydropyrido)isoindolinone Ring Systems
Synthesis (Stuttgart), Vol.50(24), pp.4837-4845
12/17/2018
DOI: 10.1055/s-0037-1610133
Abstract
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.
Details
- Title: Subtitle
- Sequential Pyridine Dearomatization–Mizoroki–Heck Cyclization for the Construction of Fused (Dihydropyrido)isoindolinone Ring Systems
- Creators
- Madhur S Joshi - Department of Chemistry, University of IowaF. Christopher Pigge - Department of Chemistry, University of Iowa
- Resource Type
- Journal article
- Publication Details
- Synthesis (Stuttgart), Vol.50(24), pp.4837-4845
- Publisher
- Georg Thieme Verlag
- DOI
- 10.1055/s-0037-1610133
- ISSN
- 0039-7881
- eISSN
- 1437-210X
- Grant note
- CHE-1265488 / U.S. National Science Foundation
- Language
- English
- Date published
- 12/17/2018
- Academic Unit
- Radiology; Chemistry
- Record Identifier
- 9984216606502771
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