Regioselective C(7)–H arylation of 2-(het)aryl [1,2,4]triazolo[1,5-a]pyrimidines by aryl halides under ruthenium catalysis

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Abstract

An unusual selectiviry of C-H arylation reactions of 2-(hetero)aryl[1,2,4]triazolo[1,5-a]pyrimidines with (hetero)aryl halides catalyzed by Ru(II) complexes was revealed. The reaction proceeds with activation of the C(7)-H bond rather than the α-C-H bond of the (hetero)aryl substituent at position 2 of the triazolopyrimidine. Arylation of 2-substituted [1,2,4]triazolo[1,5-a]pyrimidines with (hetero)aryl bromides afforded a series of 7-(hetero)arylated products in good yields.

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About the authors

K. E. Shepelenko

Platov South-Russian State Polytechnic University (NPI)

Author for correspondence.
Email: kon1990@bk.ru
ORCID iD: 0000-0002-7281-5095
Russian Federation, Prosveschenya 132, 346428 Novocherkassk

I. G. Gnatiuk

Platov South-Russian State Polytechnic University (NPI)

Email: kon1990@bk.ru
ORCID iD: 0009-0003-8772-6372
Russian Federation, Prosveschenya 132, 346428 Novocherkassk

V. M. Chernyshev

Platov South-Russian State Polytechnic University (NPI)

Email: chern13@yandex.ru
ORCID iD: 0000-0001-9182-8564
Russian Federation, Prosveschenya 132, 346428 Novocherkassk

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2. Scheme 1

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4. Figure. Schemes of key correlations in the 1H–1H NOESY spectra of compounds 2a and 2d (a), fragment of the 1H–1H NOESY spectrum of compound 2a (b)

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