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

Autor:	Padmavathi Venkatapuram, Dmitry S. Kopchuk, Albert F. Khasanov, Sougata Santra, Oleg N. Chupakhin, Sravya Gundala, Grigory V. Zyryanov, I. L. Nikonov, Emiliya V. Nosova, Adinath Majee, Igor S. Kovalev, Kousik Giri
Rok vydání:	2018
Předmět:	010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Aryne Domino 0104 chemical sciences Computational chemistry Moiety Aza-Diels–Alder reaction Domino process Inverse demand function Physical and Theoretical Chemistry
Zdroj:	Organic & Biomolecular Chemistry. 16:5119-5135
ISSN:	1477-0539 1477-0520
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4ea420ee0fd48a8b16d3093539a2dd93 https://doi.org/10.1039/c8ob00847g Zobrazit plný text záznamu