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

被引：2

作者：

Kolodina, Alexandra A. ^{[1
]}

Tsaturyan, Arshak A. ^{[1
]}

Galkina, Maria S. ^{[1
]}

Borodkina, Inna G. ^{[1
]}

Vetrova, Elena V. ^{[1
]}

Demidoy, Oleg P. ^{[2
]}

Berezhnaya, Alexandra G. ^{[3
]}

Metelitsa, Anatoly, V ^{[1
]}

机构：

[1] Southern Fed Univ, Inst Phys & Organ Chem, 194-2 Stachki St, Rostov Na Donu 344090, Russia

[2] North Caucasus Fed Univ, Dept Chem, Inst Math & Nat Sci, 1a Pushkina St, Stavropol 355009, Russia

[3] Southern Fed Univ, Fac Chem, 7 Zorge St, Rostov Na Donu 344090, Russia

来源：

CHEMISTRYSELECT | 2020年 / 5卷 / 12期

关键词：

aryl benzyl ketones; cleavage reactions; solvatochromism; tautomerism; triazolothiadiazine; TRIAZOLOTHIADIAZINE DERIVATIVES; MILD-STEEL; TRIAZOLE; THIADIAZINE; PARAMETERS;

D O I：

10.1002/slct.202000732

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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-5H-[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.

引用

页码：3586 / 3592

页数：7

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