Результаты исследований: Вклад в журнал › Статья › Рецензирование
Результаты исследований: Вклад в журнал › Статья › Рецензирование
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TY - JOUR
T1 - Transformations of 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in the reaction with an aryne intermediate
AU - Moseev, T.
AU - Idrisov, T.
AU - Lavrinchenko, I.
AU - Krinochkin, A.
AU - Kudryashova, E.
AU - Kopchuk, D.
AU - Varaksin, M.
AU - Zyryanov, G.
AU - Charushin, V.
AU - Chupakhin, O.
N1 - This work was financially supported by the Russian Science Foundation (Project No. 20-73-10077; https://rscf.ru/en/project/20-73-10077/ ).
PY - 2023/12/1
Y1 - 2023/12/1
N2 - Transformations of the various 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in their reactions with an aryne intermediate were investigated. It was shown that the interaction of a 5-unsubstituted triazine with the aryne led to an S-arylation product, whereas there were no any transformations of the pyridyltriazine system. Introduction of the pentafluorophenyl substituent at the C(6) position of the triazine changed the pathway in this reaction with the aryne, which proceeded simultaneously at two reaction centers. In particular, there were a rearrangement of the 3-(2-pyridyl)-1,2,4-triazine into the 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indole system as well as S-arylation. The product of dual functionalization, 10-{5-perfluorophenyl-4-[4-(phenylthio)phenyl]-1H-1,2,3-triazol-1-yl}pyrido[1,2-a]indole, exhibited a blue emission at λem = 395 nm and a fluorescence quantum yield comparable to the analogs obtained previously.
AB - Transformations of the various 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in their reactions with an aryne intermediate were investigated. It was shown that the interaction of a 5-unsubstituted triazine with the aryne led to an S-arylation product, whereas there were no any transformations of the pyridyltriazine system. Introduction of the pentafluorophenyl substituent at the C(6) position of the triazine changed the pathway in this reaction with the aryne, which proceeded simultaneously at two reaction centers. In particular, there were a rearrangement of the 3-(2-pyridyl)-1,2,4-triazine into the 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indole system as well as S-arylation. The product of dual functionalization, 10-{5-perfluorophenyl-4-[4-(phenylthio)phenyl]-1H-1,2,3-triazol-1-yl}pyrido[1,2-a]indole, exhibited a blue emission at λem = 395 nm and a fluorescence quantum yield comparable to the analogs obtained previously.
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U2 - 10.1007/s11172-023-4102-9
DO - 10.1007/s11172-023-4102-9
M3 - Article
VL - 72
SP - 2922
EP - 2926
JO - Russian Chemical Bulletin
JF - Russian Chemical Bulletin
SN - 1066-5285
IS - 12
ER -
ID: 52300631