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.
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页码：3586 / 3592
页数：7
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