An unusual ring contraction in the formation of N-nitrosohexamethyleneimine and N-nitrosopiperidine from tolazamide.
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.
Eshraghi
J
J
Department of Chemistry, Temple University, Philadelphia, PA 19122.
Longo
J
J
Dalton
D R
DR
Harrington
G W
GW
D002250:Carbon Radioisotopes; D055598:Chemical Phenomena; D002621:Chemistry; D009602:Nitrosamines / Q000138:chemical synthesis*; D013453:Sulfonylurea Compounds; D014042:Tolazamide
D002250:Carbon Radioisotopes; D009602:Nitrosamines; D013453:Sulfonylurea Compounds; C064837:1-(piperidyl)-3-(4-tolylsulfonyl)urea; C002743:N-nitrosopiperidine; C002742:N-nitrosoperhydroazepine; D014042:Tolazamide