Studies of Substituent Effect in the Formation of Benzonitrile Oxides and 1,3-Dipolar Adducts of the Benzonitrile Oxides with 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-glucopyranose

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概要

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• Coupling reagents were prepared from corresponding benzaldehyde oximes by successive treatment with chlorine and Et_3N; the products were used without purification because of their instability. The reactions of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose (1) with the coupling reagents obtained from benzaldehyde oxime (2a) and phenylacet-aldehyde oxime (2b) gave normal 1,3-dipolar addition products (3a and 3b, respectively) in good yields. The reactions of 1 with the coupling reagents obtained from p- (2c), m- (2d), and o-methoxybenzaldehyde oxime (2e) gave the 1,3-addition products chlorinated on the benzene ring; 3c and 3d from 2c, 3e and 3f from 2d, and 3g from 2e. On the other hand, the reactions of 1 with the coupling reagents obtained from p-chloro- (2f) and p-nitrobenzaldehyde oxime (2g) gave no 1,3-addition product.

• 社団法人日本薬学会の論文
• 1989-09-25

著者

• 斎藤 節生

  Faculty of Pharmaceutical Sciences, Josai University

• 斎藤 節生

  Faculty Of Pharmaceutical Sciences Josai University

• 鵜沢 浩

  Faculty of Pharmaceutical Sciences, Josai University

• 永次 史

  Faculty of Pharmaceutical Sciences, Josai University

• 永次 史

  Faculty Of Pharmaceutical Sciences Josai University

• 鵜沢 浩

  Faculty Of Pharmaceutical Sciences Josai University

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