One-Pot Synthesis of Benzo[4,5]imidazo[2,1‑a]isoquinolines and Isoquinolino[3,4‑b]quinoxalines via Tandem Cyclization Strategies

Two operationally simple one-pot protocols have been developed for the synthesis of amino-functionalized benzo­[4,5]­imidazo­[2,1-a]­isoquinolines and isoquinolino­[3,4-b]­quinoxalines. Optimization data and substrate scope for these atom-economical transformations, which engage commercially availab...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-05, Vol.81 (9), p.3924-3928
Main Authors: Bagdasarian, Alex L, Nguyen, Huy H, Palazzo, Teresa A, Fettinger, James C, Haddadin, Makhluf J, Kurth, Mark J
Format: Article
Language:English
Subjects:
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Catalysis
Cyclization
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Molecular Structure
Quinoxalines - chemical synthesis
Quinoxalines - chemistry
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Summary:Two operationally simple one-pot protocols have been developed for the synthesis of amino-functionalized benzo­[4,5]­imidazo­[2,1-a]­isoquinolines and isoquinolino­[3,4-b]­quinoxalines. Optimization data and substrate scope for these atom-economical transformations, which engage commercially available o-phenylenediamines and o-cyanobenzaldehydes, are discussed.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00338