Issue 28, 2018

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

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

Supplementary files

Article information

Article type
Paper
Submitted
10 Apr 2018
Accepted
24 Apr 2018
First published
24 Apr 2018

Org. Biomol. Chem., 2018,16, 5119-5135

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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