CsF-Catalyzed Transannulation Reaction of Oxazolones: Diastereoselective Synthesis of Diversified trans- N-(6-Oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with Arylidene Azlactones and Amidines

Golnaz Parhizkar; Ahmad Reza Khosropour; Iraj Mohammadpoor-Baltork; Elahehnaz Parhizkar; Hadi Amiri Rudbari

doi:10.1021/acscombsci.8b00027

CsF-Catalyzed Transannulation Reaction of Oxazolones: Diastereoselective Synthesis of Diversified trans- N-(6-Oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with Arylidene Azlactones and Amidines

ACS Comb Sci. 2018 Jun 11;20(6):358-365. doi: 10.1021/acscombsci.8b00027. Epub 2018 May 1.

Authors

Golnaz Parhizkar¹, Ahmad Reza Khosropour¹, Iraj Mohammadpoor-Baltork¹, Elahehnaz Parhizkar², Hadi Amiri Rudbari¹

Affiliations

¹ Department of Chemistry , University of Isfahan , Isfahan 81746-73441 , Iran.
² Department of Pharmaceutics, School of Pharmacy , Shiraz University of Medical Sciences , Shiraz 71468-64685 , Iran.

PMID: 29689156
DOI: 10.1021/acscombsci.8b00027

Abstract

A versatile and straightforward synthetic strategy for the construction of new tetrasubstituted 1,3-diazinones is described. The procedure is based on CsF-catalyzed, microwave-assisted, ring transformation reaction of arylidene azlactones with amidines. Moreover, this technique provides diversified trans- N-(6-oxo-1,4,5,6-tetrahydropyrimidin-5-yl)benzamides with a good antimicrobial activity.

Keywords: CsF; amidine; azlactone; diastereoselective; transannulation reaction.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Bacillus subtilis / drug effects
Benzamides / chemical synthesis*
Catalysis
Cesium / chemistry*
Escherichia coli / drug effects
Fluorides / chemistry*
Molecular Structure
Oxazolone / analogs & derivatives*
Oxazolone / chemistry*
Pyrimidines / chemical synthesis*
Staphylococcus aureus / drug effects
Stereoisomerism

Substances

Anti-Bacterial Agents
Benzamides
Pyrimidines
Oxazolone
Cesium
Fluorides
cesium fluoride