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 inOrganic & biomolecular chemistry Vol. 17; no. 39; pp. 8853 - 8857
Main Authors Gupta, Vijay, Sahu, Debashish, Jain, Shailja, Vanka, Kumar, Singh, Ravi P
Format Journal Article
Published 09.10.2019
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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.
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
1889050
1889052
and
1889053
10.1039/c9ob01345h
,
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01345h