A rapid, one-pot, microwave-influenced synthesis of spiro-2,5-diketopiperazines via a cascade Ugi/6-exo-trig aza-Michael reaction

Soumava Santra; Peter R Andreana

doi:10.1021/jo102305q

A rapid, one-pot, microwave-influenced synthesis of spiro-2,5-diketopiperazines via a cascade Ugi/6-exo-trig aza-Michael reaction

J Org Chem. 2011 Apr 1;76(7):2261-4. doi: 10.1021/jo102305q. Epub 2011 Feb 25.

Authors

Soumava Santra¹, Peter R Andreana

Affiliation

¹ Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.

PMID: 21351784
DOI: 10.1021/jo102305q

Abstract

A rapid, cascade reaction process has been developed to access biologically validated spiro-2,5-diketopiperazines. The facile and environmentally benign method capitalizes on commercially available starting reagents for a sequential Ugi/6-exo-trig aza-Michael reaction, water as a solvent, and microwave irradiation without any extraneous additives.

Publication types

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

MeSH terms

Catalysis
Crystallography, X-Ray
Diketopiperazines / chemical synthesis*
Diketopiperazines / chemistry
Indicators and Reagents / chemistry
Microwaves
Models, Molecular
Molecular Structure
Solvents / chemistry
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Stereoisomerism
Water / chemistry

Substances

Diketopiperazines
Indicators and Reagents
Solvents
Spiro Compounds
Water