TY - JOUR

T1 - Reactions of 4,5-Dimethyl-1,2-dehydrobenzene with 6-Aryl-3-(2-pyridyl)-1,2,4-triazines

AU - Rammohan, A.

AU - Guda, M.

AU - Shtaitz, Ya.

AU - Khasanov, A.

AU - Krinochkin, A.

AU - Kopchuk, D.

AU - Zyryanov, G.

AU - Rusinov, V.

N1 - This work was supported by the Russian Science Foundation (grant no. 22-73-00292).

PY - 2023

Y1 - 2023

N2 - The reactions of 5-R-6-aryl-3-(2-pyridyl)-1,2,4-triazines with a 4,5-dimethylaryne intermediate generated in situ, which had not previously been used for this purpose, was studied. The reaction outcome depends on the nature of the substituent at the C5 position of 1,2,4-triazine: the introduction of electron-donating substituents leads to the preferential domino transformation of the 3-(2-pyridyl)-1,2,4-triazine system with the formation of 2,3-dimethyl-10-(1,2,3-triazol-3-yl)pyrido[1,2-a]indoles, and electron-withdrawing ones leads to the formation of the corresponding 6,7-dimethylisoquinolines. The main difference between dimethylaryne and its unsubstituted analogue is a significant increase in the proportion of isoquinolines in the reaction products when 5,6-diaryl-3-(2-pyridyl)-1,2,4-triazines are used as substrates. © 2023, Pleiades Publishing, Ltd.

AB - The reactions of 5-R-6-aryl-3-(2-pyridyl)-1,2,4-triazines with a 4,5-dimethylaryne intermediate generated in situ, which had not previously been used for this purpose, was studied. The reaction outcome depends on the nature of the substituent at the C5 position of 1,2,4-triazine: the introduction of electron-donating substituents leads to the preferential domino transformation of the 3-(2-pyridyl)-1,2,4-triazine system with the formation of 2,3-dimethyl-10-(1,2,3-triazol-3-yl)pyrido[1,2-a]indoles, and electron-withdrawing ones leads to the formation of the corresponding 6,7-dimethylisoquinolines. The main difference between dimethylaryne and its unsubstituted analogue is a significant increase in the proportion of isoquinolines in the reaction products when 5,6-diaryl-3-(2-pyridyl)-1,2,4-triazines are used as substrates. © 2023, Pleiades Publishing, Ltd.

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UR - https://elibrary.ru/item.asp?id=64378752

U2 - 10.1134/S1070363223140256

DO - 10.1134/S1070363223140256

M3 - Article

VL - 93

SP - S94-S99

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - S1

ER -