Open chain nitrogen compounds. Part XIII. 1-Aryl-3-arylthiomethyl-3-methyltriazenes and 3-(arylazo)-1,3-thiazolidines

Reaction of 3-acetoxymethyl-1-aryl-3-methyltriazenes with sodium thiophenolate or thiocresolate in anhydrous dimethylformamide affords a new series of 3-arylthiomethyltriazenes ( 2 ), Ar-S-CH 2 -NMe-N=N-Ar′. These triazenes are remarkably labile in aqueous buffer and may be good pro-drugs for the ac...

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Bibliographic Details
Published in:Canadian journal of chemistry 1988-10, Vol.66 (10), p.2487-2491
Main Authors: Vaughan, Keith, Manning, Hartford W, Merrin, Marcus P, Hooper, Donald L
Format: Article
Language:English
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Summary:Reaction of 3-acetoxymethyl-1-aryl-3-methyltriazenes with sodium thiophenolate or thiocresolate in anhydrous dimethylformamide affords a new series of 3-arylthiomethyltriazenes ( 2 ), Ar-S-CH 2 -NMe-N=N-Ar′. These triazenes are remarkably labile in aqueous buffer and may be good pro-drugs for the active metabolite of the antitumour dimethyltriazenes. The reaction of arenediazonium fluoroborates with 1,3-thiazolidine in aqueous acetone affords a new series of N-arylazo-1,3-thiazolidines ( 4 ); the arylazothiazolidines represent a new class of triazene in which the N3 nitrogen is incorporated into a heterocyclic unit, in this case a 1,3-thiazolidine. Nuclear magnetic resonance spectra of the arylazothiazolidines show evidence for rotational isomerism of the exocyclic N2N3 bond in the triazene moiety.
ISSN:0008-4042
1480-3291
DOI:10.1139/v88-391