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丁基和糖基(2-芳氨基-4,4-二甲基-6-氧代环己-1-烯)碳二硫代酸酯的合成与X射线分析及其向2-硫代-6,7-二氢-1H-苯并[d][1,3]噻嗪-5(2H)-酮衍生物的可能环化反应

Synthesis and X-ray analysis of butyl and glycosyl (2-arylamino-4,4-dimethyl-6-oxocyclohex-1-ene)carbodithioates and their possible cyclization to 2-thioxo-6,7-dihydro-1H-benzo[d][1,3]thiazin-5(2H)-one derivatives.

作者信息

El Ashry El Sayed H, Aly Aly A, Amer Mohammed R, Shah Muhammad R, Ng Seik W

机构信息

H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.

出版信息

Carbohydr Res. 2011 Feb 1;346(2):169-76. doi: 10.1016/j.carres.2010.11.005. Epub 2010 Nov 12.

DOI:10.1016/j.carres.2010.11.005
PMID:21163469
Abstract

Variety of butyl [2-arylamino-4,4-dimethyl-6-oxo-cyclohex-1-ene]carbodithioates (3a-c), 2-thioxo-6,7-dihydro-1H-benzo[d][1,3]thiazin-5(2H)-one derivatives (5a-c), and the glucosyl carbodithioates 6a-c as well as galactosyl carbodithioates 7a-c have been synthesized from the reaction of enaminone derivatives 1a-c with carbon disulfide followed by the alkylation with n-butyl bromide and α-d-glycosyl bromides, respectively. The amount of carbon disulfide plays a great role in the mode of reaction. The structures of the synthesized compounds were elucidated by spectral data and X-ray crystallography.

摘要

通过烯胺酮衍生物1a - c与二硫化碳反应,随后分别用正丁基溴和α - d - 糖基溴进行烷基化反应,合成了多种丁基[2 - 芳基氨基 - 4,4 - 二甲基 - 6 - 氧代 - 环己 - 1 - 烯]碳二硫代酸酯(3a - c)、2 - 硫代 - 6,7 - 二氢 - 1H - 苯并[d][1,3]噻嗪 - 5(2H) - 酮衍生物(5a - c)以及葡萄糖基碳二硫代酸酯6a - c和半乳糖基碳二硫代酸酯7a - c。二硫化碳的用量在反应模式中起着重要作用。通过光谱数据和X射线晶体学对合成化合物的结构进行了阐明。

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