6,7‐Dihydro‐5 H ‐1,2,4‐triazolo[3,4‐ b ][1,3,4]thiadiazine Ring Cleavage and Tautomerism of the Products: Experimental and Theoretical Study

Electronic effects of aryl substituents at the C(7)‐atom play a crucial role in the cleavage of a six‐membered ring of 6,7‐dihydro‐5 H ‐[1,2,4]triazolo[3,4‐ b ][1,3,4]thiadiazines. Our experiments show that electron‐withdrawing 2‐nitrophenyl and 4‐nitrophenyl groups promote the N−N‐bond cleavage, wh...

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Published in:ChemistrySelect (Weinheim) 2020-03, Vol.5 (12), p.3586-3592
Main Authors: Kolodina, Alexandra A., Tsaturyan, Arshak A., Galkina, Maria S., Borodkina, Inna G., Vetrova, Elena V., Demidov, Oleg P., Berezhnaya, Alexandra G., Metelitsa, Anatoly V.
Format: Article
Language:English
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Summary:Electronic effects of aryl substituents at the C(7)‐atom play a crucial role in the cleavage of a six‐membered ring of 6,7‐dihydro‐5 H ‐[1,2,4]triazolo[3,4‐ b ][1,3,4]thiadiazines. Our experiments show that electron‐withdrawing 2‐nitrophenyl and 4‐nitrophenyl groups promote the N−N‐bond cleavage, whereas a phenyl group and a bulky 4,5‐dimethoxy‐2‐nitrophenyl substituent are favored for the C−S‐bond cleavage, affording novel triazole derivatives. UV‐vis, electrochemical, and dynamic NMR studies as well as DFT calculations of product's tautomeric equilibria were performed.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202000732