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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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