Diastereoselective multi-component tandem condensation: synthesis of 2-amino-4-(2-furanone)-4-chromene-3-carbonitriles

A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4 H -chromene-3-carbonitriles by reaction of salicylaldehyde, malononitrile and butenolides via a tandem Knoevenagel/Pinner/vinylogous Michael condensation is presented. The β,γ-butenolides gave a syn -selective MCR...

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Published in:Organic & biomolecular chemistry 2019-10, Vol.17 (39), p.8853-8857
Main Authors: Gupta, Vijay, Sahu, Debashish, Jain, Shailja, Vanka, Kumar, Singh, Ravi P
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Summary:A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4 H -chromene-3-carbonitriles by reaction of salicylaldehyde, malononitrile and butenolides via a tandem Knoevenagel/Pinner/vinylogous Michael condensation is presented. The β,γ-butenolides gave a syn -selective MCR adduct with a dr up to 11.5 : 1. The mechanistic insight into the MCR was obtained by DFT calculations. Highly syn -selective unification of three components (salicylaldehyde, malononitrile and butenolides) in the presence of sodium tert -butoxide has been realised. The reaction proceeds via a tandem Knoevenagel/Pinner/vinylogous Michael condensation.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01345h