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 beta,gamma-butenolides gave a syn-selective...

Full description

Saved in:
Bibliographic Details
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
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.10.2019
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Condensation
Crystallography
Malononitrile
Physical Sciences
Science & Technology
Stereoselectivity
CHEMISTRY
ALDEHYDES
NATURAL-PRODUCT SYNTHESIS
DERIVATIVES
GREEN
ACCESS
Online AccessGet full text

Cover

More Information
Summary: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 beta,gamma-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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob01345h