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Int. J. Mol. Sci. 2013, 14(6), 12484-12495; doi:10.3390/ijms140612484
Article

Facile Synthesis of 5-Arylidene Thiohydantoin by Sequential Sulfonylation/Desulfination Reaction

1
,
1
,
1,2
,
1
 and
1,*
1 Department of Applied Chemistry, China Agricultural University, Beijing 100193, China 2 College of Agriculture, Yangtze University, Jingzhou 434025, Hubei, China
* Author to whom correspondence should be addressed.
Received: 6 May 2013 / Revised: 28 May 2013 / Accepted: 29 May 2013 / Published: 13 June 2013
(This article belongs to the Section Molecular Toxicology)
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Abstract

The sequential sulfonylation/desulfination reactions of 5-benzylthiohydantoin with excess arylsulfonyl chlorides in the presence of triethylamine have been developed to afford a wide range of 5-arylidene thiohydantoin derivatives in moderate to excellent yields. A plausible sulfonylation/desulfination mechanism was proposed. The bioassay showed that these compounds exhibit certain fungicidal activities with the 71.9% inhibition rate of 2K against B. cinerea, and 57.6% inhibition rate of 2m against A. solani, respectively.
Keywords: 5-arylidene thiohydantoin; sulfonylation; desulfination; arylsulfonyl chloride 5-arylidene thiohydantoin; sulfonylation; desulfination; arylsulfonyl chloride
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Han, J.; Dong, H.; Xu, Z.; Lei, J.; Wang, M. Facile Synthesis of 5-Arylidene Thiohydantoin by Sequential Sulfonylation/Desulfination Reaction. Int. J. Mol. Sci. 2013, 14, 12484-12495.

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