Open AccessAn Unusual Ring Contraction in the Formation of N‐Nitrosohexamethyleneimine and N‐Nitrosopiperidine from Tolazamide
Author(s) -
Eshraghi Jamshid,
Longo John,
Dalton David R.,
Harrington George W.
Publication year - 1990
Publication title -
japanese journal of cancer research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.035
H-Index - 141
eISSN - 1349-7006
pISSN - 0910-5050
DOI - 10.1111/j.1349-7006.1990.tb02570.x
Subject(s) - chemistry , contraction (grammar) , nitrite , ring (chemistry) , stereochemistry , medicine , organic chemistry , nitrate
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.