An efficient and facile synthesis of 3-amino-5-chromenyl-butenolides from 3-formyl chromone, dialkyl acetylenedicarboxylate, and primary amines

Saeed Balalaie; Morteza Ashouriha; Frank Rominger; Hamid Reza Bijanzadeh

doi:10.1007/s11030-013-9423-4

An efficient and facile synthesis of 3-amino-5-chromenyl-butenolides from 3-formyl chromone, dialkyl acetylenedicarboxylate, and primary amines

Mol Divers. 2013 Feb;17(1):55-61. doi: 10.1007/s11030-013-9423-4. Epub 2013 Jan 23.

Authors

Saeed Balalaie¹, Morteza Ashouriha, Frank Rominger, Hamid Reza Bijanzadeh

Affiliation

¹ Peptide Chemistry Research Center, KN Toosi University of Technology, Tehran, Iran. balalaie@kntu.ac.ir

PMID: 23341007
DOI: 10.1007/s11030-013-9423-4

Abstract

A three-component reaction of 3-formyl chromones, dialkyl acetylenedicarboxylate, and isocyanides in the presence of POCl(3) was used as a highly efficient and practical approach for the synthesis of 3-amino-5-chromenyl-butenolides. High yields and high bond forming efficiency, and simple operations are the advantages of this method. Graphical abstract.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis
Alkynes / chemistry*
Amines / chemistry*
Chromones / chemistry*
Cyanides / chemistry
Fatty Acids, Unsaturated / chemistry*

Substances

Alkynes
Amines
Chromones
Cyanides
Fatty Acids, Unsaturated
2-butynedioic acid
butenolide
4-Butyrolactone