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NH 4 OAc‐Promoted Cascade Approach towards Aberrant Synthesis of Chromene‐Fused Quinolinones
Author(s) -
Kumari Santosh,
Shakoor S. M. Abdul,
Markad Datta,
Mandal Sanjay K.,
Sakhuja Rajeev
Publication year - 2019
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.201801292
Subject(s) - chemistry , coumarin , formylation , ammonium acetate , cascade , combinatorial chemistry , aryl , cascade reaction , organic chemistry , catalysis , chromatography , alkyl , high performance liquid chromatography
A concise cascade strategy for the synthesis of 6 H ‐chromeno[4,3‐ b ]quinolin‐6‐ones was developed from 4‐hydroxycoumarins and arylhydrazine hydrochlorides in DMSO. The synthetic strategy relies on dual role of ammonium acetate in generating 4‐aminophenyl coumarin from arylhydrazine via aryl radical formation, and Csp 2 ‐H formylation of coumarin using DMSO as a methine source. The strategy is scalable, and an array of arylhydrazine hydrochlorides delivered chromene‐fused quinolinones in good to excellent yields.