Traceless synthesis of 3-N-substituted-2-thioxoquinazoline-4-ones on a soluble polymeric support

Hongdan Peng; Yanling Huang; Jianhong Yang; Zuxing Chen; Guichun Yang

doi:10.2174/138620707780636664

Traceless synthesis of 3-N-substituted-2-thioxoquinazoline-4-ones on a soluble polymeric support

Comb Chem High Throughput Screen. 2007 May;10(4):257-60. doi: 10.2174/138620707780636664.

Authors

Hongdan Peng¹, Yanling Huang, Jianhong Yang, Zuxing Chen, Guichun Yang

Affiliation

¹ Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Faculty of Chemistry and Chemical Engineering, Hubei University, Wuhan, Hubei, PR China.

PMID: 17506708
DOI: 10.2174/138620707780636664

Abstract

The synthesis of 3-N-substituted-2-thioxoquinazoline-4-ones is described with a traceless linker strategy using poly(ethylene glycol) (PEG) as a soluble polymeric support. Staudinger-Aza-Wittig reaction of PEG-supported azide with Ph(3)P and CS(2) gave the corresponding PEG-supported phenyl isothiocyanate. Treatment of the phenyl isothiocyanate with different primary amines led, via intramolecular cyclization and simultaneous cleavage from PEG, to 2-thioxoquinazoline-4-ones with of moderate to excellent yields.

Publication types

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

MeSH terms

Molecular Structure
Polyethylene Glycols / chemistry*
Quinazolinones / chemical synthesis*
Quinazolinones / chemistry
Solubility

Substances

Quinazolinones
Polyethylene Glycols