Transformations of 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in the reaction with an aryne intermediate

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Transformations of 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in the reaction with an aryne intermediate. / Moseev, T.; Idrisov, T.; Lavrinchenko, I. et al.
In: Russian Chemical Bulletin, Vol. 72, No. 12, 01.12.2023, p. 2922-2926.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{d727737f1b5f40ada270ca60a9acce6b,

title = "Transformations of 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in the reaction with an aryne intermediate",

abstract = "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.",

author = "T. Moseev and T. Idrisov and I. Lavrinchenko and A. Krinochkin and E. Kudryashova and D. Kopchuk and M. Varaksin and G. Zyryanov and V. Charushin and O. Chupakhin",

note = "This work was financially supported by the Russian Science Foundation (Project No. 20-73-10077; https://rscf.ru/en/project/20-73-10077/ ).",

year = "2023",

month = dec,

day = "1",

doi = "10.1007/s11172-023-4102-9",

language = "English",

volume = "72",

pages = "2922--2926",

journal = "Russian Chemical Bulletin",

issn = "1066-5285",

publisher = "Springer",

number = "12",

}

RIS

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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UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001154671000004

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