Hexachlorocyclotriphosphazene (HCCP)-mediated direct formation of thioethers and ethers from quinazolin-4(3H)-ones

Baoxiang Hu; Xiaochu Zhang; Lili Sheng; Ming Guo; Zhenlu Shen; Xinquan Hu; Nan Sun; Weimin Mo

doi:10.3390/molecules18055580

Hexachlorocyclotriphosphazene (HCCP)-mediated direct formation of thioethers and ethers from quinazolin-4(3H)-ones

Molecules. 2013 May 15;18(5):5580-93. doi: 10.3390/molecules18055580.

Authors

Baoxiang Hu¹, Xiaochu Zhang, Lili Sheng, Ming Guo, Zhenlu Shen, Xinquan Hu, Nan Sun, Weimin Mo

Affiliation

¹ State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, China.

Abstract

A hexachlorocyclotriphosphazene (HCCP)-mediated direct formation of quinazoline (thio)ethers from quinazolin-4(3H)-ones has been developed. Treatment of quinazolin-4(3H)-ones with HCCP, diisopropylethylamine (DIPEA), and thiophenols resulted in formation of the corresponding 4-arylthioquinazoline derivatives in moderate to excellent yields. This method has also been utilized to prepare 4-aryloxyquinazoline and 4-alkoxyquinazoline derivatives using phenols and sodium alkoxides as the nucleophiles.

Publication types

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

MeSH terms

Ethers / chemical synthesis*
Ethers / chemistry*
Phosphoranes / chemistry*
Quinazolines / chemistry*

Substances

Ethers
Phosphoranes
Quinazolines
hexachlorocyclotriphosphazene