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An Unusual Ring Contraction in the Formation of NâNitrosohexamethyleneimine and NâNitrosopiperidine 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 Nânitrosohexamethyleneimine and surprisingly, Nânitrosopiperidine was confirmed. By using the sixâmembered ring analogue of tolazamide, 1â(piperidyl)â3â(pâtolylsulfonyl)urea, which yields the corresponding Nânitrosopiperidine and Nânitrosopyrrolidine, the present study shows that an unusual ring contraction occurs, excising the carbon alpha to the nitrogen.
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Eshraghi, J., Longo, J., Dalton, D.R. and Harrington, G.W. (1990), An Unusual Ring Contraction in the Formation of NâNitrosohexamethyleneimine and NâNitrosopiperidine 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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