Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 28, Pages -Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob00847g
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Funding
- Russian Science Foundation [18-13-00365]
- DST-RSF Major Research Project [INT/RUS/RSF/P-08]
- DST, Govt. of India [YSS/2014/000060]
- Russian Science Foundation [18-13-00365] Funding Source: Russian Science Foundation
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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.
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