The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of primary amines: synthesis of alkyl 2-benzoyl-4-alkylamino-5-oxo-2,5-dihydro-3-furan carboxylate derivatives

Authors

JAVAD SAFAEI GHOMI
FARIBA SALIMI
ALI RAMAZANI
FATEMEH ZEINALI NASRABADI
YAVAR AHMADI

DOI

10.3906/kim-1109-40

Abstract

A 3-component domino reaction approach between a primary amine, a dialkyl acetylenedicarboxylate, and 2-oxo-2- phenylacetaldehyde that affords novel alkyl 2-benzoyl-4-alkylamino- 5-oxo-2,5-dihydro-3-furan carboxylate derivatives is reported. The reaction sequence consists of an initial Michael addition of primary amines to dialkyl acetylenedicarboxylates, followed by an aldol-like reaction with 2-oxo-2-phenylacetaldehyde, and then \gamma -lactonization to afford the products. This cascade reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.

Keywords

Dialkyl acetylenedicarboxylates, 2-oxo-2-phenylacetaldehyde, primary amines, furan, Michael addition

First Page

485

Last Page

492

Recommended Citation

GHOMI, JAVAD SAFAEI; SALIMI, FARIBA; RAMAZANI, ALI; NASRABADI, FATEMEH ZEINALI; and AHMADI, YAVAR (2012) "The reaction of dialkyl acetylenedicarboxylates with 2-oxo-2-phenylacetaldehyde in the presence of primary amines: synthesis of alkyl 2-benzoyl-4-alkylamino-5-oxo-2,5-dihydro-3-furan carboxylate derivatives," Turkish Journal of Chemistry: Vol. 36: No. 3, Article 12. https://doi.org/10.3906/kim-1109-40
Available at: https://journals.tubitak.gov.tr/chem/vol36/iss3/12