Substrate-Controlled Divergent Synthesis of Benzimidazole-Fused Quinolines and Spirocyclic Benzimidazole-Fused Isoindoles.

Autor:	Huang YT; Department of Applied Chemistry, National Yang Ming Chiao Tung University, 1001 Ta-Hsueh Road, Hsinchu 300-10, Taiwan ROC., Huang WW; Department of Applied Chemistry, National Yang Ming Chiao Tung University, 1001 Ta-Hsueh Road, Hsinchu 300-10, Taiwan ROC., Huang YT; Department of Applied Chemistry, National Yang Ming Chiao Tung University, 1001 Ta-Hsueh Road, Hsinchu 300-10, Taiwan ROC., Chen HR; Department of Applied Chemistry, National Yang Ming Chiao Tung University, 1001 Ta-Hsueh Road, Hsinchu 300-10, Taiwan ROC., Barve IJ; Department of Chemistry, MES Abasaheb Garware College, Pune 411004, Maharashtra India., Sun CM; Department of Applied Chemistry, National Yang Ming Chiao Tung University, 1001 Ta-Hsueh Road, Hsinchu 300-10, Taiwan ROC.; Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, 100, Shih-Chuan first Road, Kaohsiung 807-08, Taiwan ROC.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2024 Jun 07; Vol. 89 (11), pp. 7513-7520. Date of Electronic Publication: 2024 May 09.
DOI:	10.1021/acs.joc.4c00164
Abstrakt:	A Rh(III)-catalyzed annulation of 2-arylbenzimidazoles with α-diazo carbonyl compounds via C-H activation/carbene insertion/intramolecular cyclization is explored. The switchable product selectivity is achieved by the use of distinct α-diazo carbonyl compounds. Benzimidazole-fused quinolines are obtained through [4 + 2] annulation exclusively when 2-diazocyclohexane-1,3-diones are used, where they act as a C2 synthon. Alternatively, diazonaphthalen-1(2 H )-ones merely function as a one-carbon unit synthon to generate a quaternary center through [4 + 1] cyclization to afford spirocyclic benzimidazole-fused isoindole naphthalen-2-ones. A thorough mechanistic study reveals the course of the reaction.
Databáze:	MEDLINE
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