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Molecules 2013, 18(5), 5580-5593; doi:10.3390/molecules18055580
Article

Hexachlorocyclotriphosphazene (HCCP)-Mediated Direct Formation of Thioethers and Ethers from Quinazolin-4(3H)-ones

1, 1, 1, 2, 1,* , 1, 1 and 1,*
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 2 Department of Chemistry, Zhejiang Agriculture & Forestry University, Lin'An 311300, China
* Authors to whom correspondence should be addressed.
Received: 25 March 2013 / Revised: 12 May 2013 / Accepted: 13 May 2013 / Published: 15 May 2013
(This article belongs to the Section Organic Synthesis)
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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.
Keywords: quinazolin-4(3H)-ones; hexachlorocyclotriphosphazene; 4-arylthioquinazolines; 4-aryloxyquinazolines; 4-alkoxyquinazolines quinazolin-4(3H)-ones; hexachlorocyclotriphosphazene; 4-arylthioquinazolines; 4-aryloxyquinazolines; 4-alkoxyquinazolines
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Hu, B.; Zhang, X.; Sheng, L.; Guo, M.; Shen, Z.; Hu, X.; Sun, N.; Mo, W. Hexachlorocyclotriphosphazene (HCCP)-Mediated Direct Formation of Thioethers and Ethers from Quinazolin-4(3H)-ones. Molecules 2013, 18, 5580-5593.

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