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The regiospecific N-sulfonylation and N-phosphorylation of benzoyl-substituted heterocyclic ketene aminals

✍ Scribed by Zhan-Jiang Li; Zhong-Xu Ren; Zhi-Tang Huang

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 143 KB
Volume: 10
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(1999)10:4<297::aid-hc6>3.0.co;2-r

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✦ Synopsis

The regiospecific N-sulfonylation and N-phosphorylation of benzoyl-substituted heterocyclic ketene aminals have been investigated. In the presence of sodium hydride, benzoyl-substituted heterocyclic ketene aminals 1 or 2 reacted with p-toluenesulfonyl chloride 3 to give (E)-1-(p-toluenesulfonyl)-2-(aroylmethylene)imidazolidine 4 or (E)-1-(p-toluenesulfonyl)-2-(aroylmethylene)hexahydropyrimidine 5, respectively. Under the same condition, 1 reacted with diethyl chlorothiophosphate 6 to give diethyl [2-(aroylmethylene)imidazolidin-1-yl]thiophosphate 7. However, 2 failed to react with 6 to give N-phosphorylated products.

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