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Synthesis and research of cis-trans isomerism for 5-(4-methoxybenzoyl)-6-(4-metoxyphenyl)-6,7-dihydro-5H-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine

T. A. Kalinina, O. A. Bystrykh, J. S. Shakhmina, T. V. Glukhareva, Zhi-Jin Fan, Yu. Yu. Morzherin


It was shown that the reaction of 1,2,3-4-methoxybenzaldehyde tiadiazolyl hydrazona and α-bromo-4-methoxyacetophenone in the presence of triethylamine allowes 5-(4-methoxybenzoyl)-6-(4-methoxyphenyl)-6,7-dihydro-5H-[1,2,3]triazolo[5,1-b][1,3,4]thiadiazine as a mixture of cis- and trans-stereoisomers. The influence of nature of the solvent and temperature on the ratio of isomers was studied. An increase of the relative amount of the trans-stereoisomer with increasing polarity of the solvent is disclosed. It is noted that the temperature does not affect the ratio of isomers.


1,2,3-thiadiazole; Dimroth rearrangement; thiadiazine; isomerism; effect of temperature; solvent


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Kalinina TA, Prokhorova PE, Glukhareva TV, Morzherin YuYu. Phosphorus pentachloride-induced transformation of (1,2,3-thiadiazol-5-yl) hydrazones of acetophenone. Russ Chem Bull. 2011;60(5):981-4. doi:10.1007/s11172-011-0154-3

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Morzherin YuYu, Glukhareva TV, Bakulev VA. Rearrangements and transformations of 1,2,3-thiadiazoles in organic synthesis. Chem Heterocyc Compd. 2003;39(6):679-706. doi:10.1023/A:1025689208261

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Copyright (c) 2014 T. A. Kalinina, O. A. Bystrykh, J. S. Shakhmina, T. V. Glukhareva, Zhi-Jin Fan, Yu. Yu. Morzherin

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Chimica Techno Acta, 2014-2023
ISSN 2411-1414 (Online)
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