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An Unusual Ring Contraction in the Formation of N‐Nitrosohexamethyleneimine and N‐Nitrosopiperidine from Tolazamide
Eshraghi, Jamshid Longo, John Dalton, David R. Harrington, George W.
Eshraghi, Jamshid
Longo, John
Dalton, David R.
Harrington, George W.
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Journal article
Date
1990-04
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Chemistry
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https://doi.org/10.1111/j.1349-7006.1990.tb02570.x
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.
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Citation
Eshraghi, J., Longo, J., Dalton, D.R. and Harrington, G.W. (1990), An Unusual Ring Contraction in the Formation of N‐Nitrosohexamethyleneimine and N‐Nitrosopiperidine from Tolazamide. Japanese Journal of Cancer Research, 81: 324-326. https://doi-org/10.1111/j.1349-7006.1990.tb02570.x
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Wiley
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Japanese Journal of Cancer Research, Vol. 81, Iss. 4
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