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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 12
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Original Articles

General and Green Synthesis of C-6 Sulfonylmethyl 4-Aryl-3,4-dihydropyrimidinones in Water

Zheng-Jun Quan Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, China
,
Qiang-Bing Wei Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, China
,
Dong-Dong Ma Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, China
,
Yu-Xia Da Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, China
,
Xi-Cun Wang Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, ChinaCorrespondence[email protected]
&
Mao-Sen Shen Jing Tai Second Middle School, Baiyin, Gansu, China
Pages 2230-2239 | Received 22 Aug 2008, Published online: 12 May 2009
 
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Abstract

A simple, inexpensive, and green reaction permitting the synthesis of new C-6 arylsulfonylmethyl 4-aryl-3,4-dihydropyrimidinones in water by S-alkylation of 6-bromomethyl 3,4-dihydropyrimidinones 2 with benzenesulfinic acid anions 3 is reported. The required 6-bromomethyldihydropyrimidone precursors 2 were readily prepared using an organic solid brominating reagent.

ACKNOWLEDGMENT

We are thankful for the financial support from the Natural Science Foundation of Gansu Province (3ZS061-A25-019) and the Scientific Research Fund of Gansu Provincial Education Department (0601-25).

Notes

a Reaction conditions: a mixture of 1 equiv. of 2a with 2 equiv. of 3a was heated under reflux condtions for 24 h.

b Isolated yield.

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