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