Catalyst-Free One-Pot Synthesis of Chromeno-Imidazo-Pyridinones by an Aza-Michael Addition/Rearrangement/Heterocyclization Tandem Reaction
authors Lakhdari, H; Talhi, O; Hassaine, R; Taibi, N; Mendes, RF; Paz, FAA; Bennamane, N; Nedjar-Kolli, B; Bachari, K; Silva, AMS
nationality International
journal SYNLETT
author keywords chromones; ethanediamine; chromeno-imidazo-pyridinones; one-pot synthesis; tandem reaction; aza-Michael addition
keywords CRIBROSTATIN-6; HETEROCYCLES; RIFAXIMIN; ZOLPIDEM; RECEPTOR; ACCESS; AGENTS
abstract A one-pot synthesis of a novel series of chromeno-imidazo-pyridinone derivatives from 3-[(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]chromones and ethane-1,2-diamine at room temperature under catalyst-free conditions has been successfully developed. This approach involves a tandem aza-Michael addition reaction, a chromone-to-chromanone rearrangement, and a heterocyclization sequence, leading to chromeno-imidazo-pyridinone polyheterocycles. The structure and absolute configurations of the new compounds were elucidated by a combination of 1D- and 2D-NMR analyses and single-crystal X-ray diffraction.
publisher GEORG THIEME VERLAG KG
issn 0936-5214
year published 2018
volume 29
issue 11
beginning page 1437
ending page 1440
digital object identifier (doi) 10.1055/s-0037-1609684
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000435602300005
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journal impact factor 2.369
5 year journal impact factor 2.018
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