Open AccessThe regiospecific N ‐sulfonylation and N ‐phosphorylation of benzoyl‐substituted heterocyclic ketene aminals
Author(s) -
Li ZhanJiang,
Ren ZhongXu,
Huang ZhiTang
Publication year - 1999
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/(sici)1098-1071(1999)10:4<297::aid-hc6>3.0.co;2-r
Subject(s) - ketene , chemistry , benzoyl chloride , sodium hydride , heteroatom , imidazolidine , medicinal chemistry , phosphorylation , organic chemistry , ring (chemistry) , biochemistry
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. © 1999 John Wiley & Sons, Inc. Heteroatom Chem 10: 297–301, 1999