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. ...
![1,3,4-Thiadiazole-2(3H)-thione,5-[[(4-methyl-3-oxido-2-quinazolinyl)methyl]thio]- Structure](https://image.chemsrc.com/caspic/284/6965-89-5.png)
![Quinazoline,2-[(2-benzothiazolylthio)methyl]-4-methyl-, 3-oxide Structure](https://image.chemsrc.com/caspic/022/6965-83-9.png)