Attack of S??vs N??Nucleophiles on 2??halomethylquinazoline 3??Oxides

HS Broadbent, RC Anderson…

Index: Smith Broadbent,H. et al. Journal of Heterocyclic Chemistry, 1977 , vol. 14, p. 289 - 297

Full Text: HTML

Citation Number: 4

Abstract

Abstract A comparison is made of thiols with amines in their mode of reaction with different substituted 2-halomethylquinazoline 3-oxides. Whereas the reaction of some amines (particularly small primary ones), as has long been known, leads to ring-enlarging rearrangement under certain conditions, all thiol nucleophiles we have observed, ranging from small to large, lead without rearrangement to direct benzylic substitution only. ...