Regioselectivite Synthesis, Structure and Biological Activity of Novel 2,3-Dihydro-2-substitutionalsulfonylhydrazono-3-per-O-acetylglycosyl Thiazoles

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (05): 703-706. Previous Articles Next Articles

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区域选择性合成2-取代磺酰基亚肼基-3-全乙酰糖基-2,3-二氢噻唑及其表征、生物活性研究

王浩安，李玉新，李一鸣，王素华，李正名*

(南开大学元素有机化学国家重点实验室天津 300071)

收稿日期:2009-08-10 修回日期:2009-10-21 发布日期:2009-12-15
通讯作者: 李正名 E-mail:nkzml@vip.163.com;nkzml@finechembio.cn
基金资助:
天津市自然科学基金重点项目

Regioselectivite Synthesis, Structure and Biological Activity of Novel 2,3-Dihydro-2-substitutionalsulfonylhydrazono-3-per-O-acetylglycosyl Thiazoles

WANG Hao-An, LI Yu-Xin, LI Yi-Ming, WANG Su-Hua, LI Zheng-Ming

(State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071)

Received:2009-08-10 Revised:2009-10-21 Published:2009-12-15

Abstract

A series of novel 2,3-dihydro-2-phenylsulfonylhydrazono-3-per-O-acetylglycosyl thiazoles were designed and synthesized via reaction of the chloroacetaldehyde with 1-arylsulfonyl-4-per-O-acetylglyco- sylthiosemicarbazides, which were synthesized via condensation of per-O-acetylglycosthiocyanate with substituted phenylsulfonylhydrazines. Their chemical structures were characterized by ¹H NMR, ¹³C NMR and elemental analysis. ¹H-¹³C HMBC of compound 3e revealed the exclusive regioselectivity of these ring closures toward the N-4 position of the thiosemicarbazide moiety. The bioassaay data indicated that this type of novel compounds showed some herbicidal activity.

Key words: ¹H-¹³C HMBC correlation spectra, regioselectivity, 2,3-dihydrothiazoles

Cite this article

WANG Hao-An, LI Yu-Xin, LI Yi-Ming, WANG Su-Hua, LI Zheng-Ming. Regioselectivite Synthesis, Structure and Biological Activity of Novel 2,3-Dihydro-2-substitutionalsulfonylhydrazono-3-per-O-acetylglycosyl Thiazoles[J]. Chin. J. Org. Chem., 2010, 30(05): 703-706.

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区域选择性合成2-取代磺酰基亚肼基-3-全乙酰糖基-2,3-二氢噻唑及其表征、生物活性研究

Regioselectivite Synthesis, Structure and Biological Activity of Novel 2,3-Dihydro-2-substitutionalsulfonylhydrazono-3-per-O-acetylglycosyl Thiazoles

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