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

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

A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4H-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 ad...

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Veröffentlicht in:Organic & biomolecular chemistry 2019-10, Vol.17 (39), p.8853-8857
Hauptverfasser: Gupta, Vijay, Sahu, Debashish, Jain, Shailja, Vanka, Kumar, Singh, Ravi P
Format: Artikel
Sprache:eng
Schlagworte:
Condensation
Crystallography
Malononitrile
Stereoselectivity
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Zusammenfassung:A general strategy for a one-pot stereoselective synthesis of 2-amino-4-(2-furanone)-4H-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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01345h