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Ir(III)-Catalyzed [4 + 2] cyclization of azobenzene and diazotized Meldrum's acid for the synthesis of cinnolin-3(2H)-one

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Abstract

The first report on Ir(III)-catalyzed C–H alkylation/cyclization of azobenzene with diazotized Meldrum's acid is described for the synthesis of cinnolin-3(2H)-one derivatives under mild conditions. Controlled experiments led to the isolation of intermediate ortho-alkylated product of azobenzene, which was converted to both cinnolin-3(2H)-one-4-carboxylic acid and its ester derivative. Additionally, the iridacyclic complex of azobenzene was isolated and found to be an active intermediate in the catalytic cycle.

Graphical abstract: Ir(iii)-Catalyzed [4 + 2] cyclization of azobenzene and diazotized Meldrum's acid for the synthesis of cinnolin-3(2H)-one

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Publication details

The article was received on 29 Dec 2018, accepted on 06 Feb 2019 and first published on 06 Feb 2019


Article type: Paper
DOI: 10.1039/C8OB03214A
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Ir(III)-Catalyzed [4 + 2] cyclization of azobenzene and diazotized Meldrum's acid for the synthesis of cinnolin-3(2H)-one

    G. Borah and P. Patel, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C8OB03214A

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