A versatile domino process for the synthesis of substituted 3-aminomethylene-chromanones and 2-pyridones catalyzed by CsF.

Authors :: Pintiala, Catalin
Lawson, Ata Martin
Comesse, Sébastien
Daïch, Adam
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. May2013, Vol. 54 Issue 22, p2853-2857. 5p.
Publication Year :: 2013
Abstract: Abstract: The addition of various primary amines onto 3-α,β-unsaturated diester chromone derivative was studied under mild conditions. Basically, this reaction provided 2-pyridone-based compounds through an interesting domino ‘Addition/Ring Opening/Ring Closure’ process (ARORC). In this study, aniline and tryptamine series exhibited different reactivity profiles leading unexpectedly to 3-aminomethylene chromanones with or without the 2-pyridone derivatives. This constitutes the first description and study of 3-aminomethylene chromanone formation that is supposed to follow a domino process combining ‘Addition/Ring Opening/Ring Closure by Oxa-Michael addition’ (ARORCOM). [Copyright &y& Elsevier]

Subjects :: *AMINES
*UNSATURATED compounds
*CHROMONES
*CHEMICAL derivatives
*TRYPTAMINE
*REACTIVITY (Chemistry)

Language :: English
ISSN :: 00404039
Volume :: 54
Issue :: 22
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 89071594
Full Text :: https://doi.org/10.1016/j.tetlet.2013.03.096

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