Sankararaman, Sethuraman ; Ramkumar, Venkatachalam ; Chandrasekhar, Attoor (2018) Palladium catalyzed carbonylative annulation of C(sp2)-H bond of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-triazol-3-amines to quinazolinones. Organic & Biomolecular Chemistry, 16 . ISSN 1477-0520
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Official URL: https://doi.org/10.1039/C8OB02516A
Related URL: http://dx.doi.org/10.1039/C8OB02516A
Abstract
Pd(II) catalyzed direct C-H carbonylative annulation of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-1,2,4-triazol-3-amines gave the corresponding triazole and tetrazole fused quinazolinones in good yields. This methodology offers a convenient method for the synthesis of these important heterocyclic scaffold in a highly atom economic process. On the mechanistic aspect weakly nucleophilic triazole and tetrazole moieties function as both directing as well as intramolecular nucleophiles. The catalytically active C-H activated intermediate dimeric Pd complex was isolated and characterized which on exposure to CO gas gave the corresponding tetrazole fused quinazolinone derivative. On the basis of isolation of the intermediate and observed kinetic isotope effects, a mechanism has been proposed for the C-H activated direct carbonylative annulation reaction.
Item Type: | Article |
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Source: | Copyright of this article belongs to Royal Society of Chemistry. |
ID Code: | 124309 |
Deposited On: | 12 Nov 2021 11:49 |
Last Modified: | 12 Nov 2021 11:49 |
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