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Rhodium(II)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: a combined experimental and computational study

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Abstract

The Rh(II)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes leading to the octahydro-1H-purine derivatives with moderate to good yields is described in this communication. Mechanistic studies via DFT calculations suggest that the 1,3,5-triazinanes might undergo a formal [6+3] cycloaddition with the Rh(II)-azavinyl carbene intermediates, which are generated from Rh(II)-catalyzed denitrogenation of 1,2,3-triazoles. Afterwards, ring-closure of the formed nine-membered ring intermediate via intramolecular nucleophilic addition followed by subsequent rearrangements could afford the final octahydro-1H-purine derivatives.

Graphical abstract: Rhodium(ii)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: a combined experimental and computational study

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Publication details

The article was received on 24 Mar 2019, accepted on 28 Apr 2019 and first published on 29 Apr 2019


Article type: Communication
DOI: 10.1039/C9CC02294E
Chem. Commun., 2019, Advance Article

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    Rhodium(II)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: a combined experimental and computational study

    J. Ge, X. Wu and X. Bao, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC02294E

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