Eshraghi J, Longo J, Dalton D R, Harrington G W
Department of Chemistry, Temple University, Philadelphia, PA 19122.
Jpn J Cancer Res. 1990 Apr;81(4):324-6. doi: 10.1111/j.1349-7006.1990.tb02570.x.
The previously reported reaction of tolazamide with nitrite, under physiological conditions, to form N-nitrosohexamethyleneimine and surprisingly, N-nitrosopiperidine was confirmed. By using the six-membered ring analogue of tolazamide, 1-(piperidyl)-3-(p-tolylsulfonyl)urea, which yields the corresponding N-nitrosopiperidine and N-nitrosopyrrolidine, the present study shows that an unusual ring contraction occurs, excising the carbon alpha to the nitrogen.
已证实，在生理条件下，甲苯磺丁脲与亚硝酸盐反应生成N-亚硝基六亚甲基亚胺，令人惊讶的是，还生成了N-亚硝基哌啶。通过使用甲苯磺丁脲的六元环类似物1-(哌啶基)-3-(对甲苯磺酰基)脲，该类似物会生成相应的N-亚硝基哌啶和N-亚硝基吡咯烷，本研究表明发生了异常的环收缩，切除了氮原子α位的碳原子。
