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Issue 28, 2018
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Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels–Alder reaction versus aryne-mediated domino process

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Abstract

The interactions between substituted 5-R-3-(pyridyl-2)-1,2,4-triazines with in situ generated substituted aryne intermediates have been studied. The reaction afforded either inverse demand (ID) aza-Diels–Alder products or 1,2,4-triazine ring rearrangement (domino) products as major ones depending on the nature of both the substituents at the C5 position of the 1,2,4-triazine core or in the aryne moiety. The structures of the key products were confirmed based on X-ray data. Based on the density functional theoretical (DFT) studies of the Diels–Alder transition state geometries, the influence of the nature of arynes on the direction of the 1,2,4-triazine transformation has been proposed.

Graphical abstract: Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels–Alder reaction versus aryne-mediated domino process

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Publication details

The article was received on 10 Apr 2018, accepted on 24 Apr 2018 and first published on 24 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00847G
Org. Biomol. Chem., 2018,16, 5119-5135

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    Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels–Alder reaction versus aryne-mediated domino process

    D. S. Kopchuk, I. L. Nikonov, A. F. Khasanov, K. Giri, S. Santra, I. S. Kovalev, E. V. Nosova, S. Gundala, P. Venkatapuram, G. V. Zyryanov, A. Majee and O. N. Chupakhin, Org. Biomol. Chem., 2018, 16, 5119
    DOI: 10.1039/C8OB00847G

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