Amidative Cyclization of Alkynyl Esters to Access Pyrazin-1(2 H )-ones: Application to the Synthesis of Peramine and Dibromophakellin.

Autor:	Gangnale LD; Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Miriyala SRT; Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Pasunooti KK; Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India.; Department of Pharmacology and Molecular Sciences, Johns Hopkins School of Medicine, Baltimore, Maryland 21205, United States., Reddy DS; Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.; Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2023 Dec 15; Vol. 88 (24), pp. 17330-17344. Date of Electronic Publication: 2023 Dec 05.
DOI:	10.1021/acs.joc.3c02157
Abstrakt:	Herein, we report an efficient 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed tandem intermolecular amidation and regioselective intramolecular 6- exo -dig cyclization of alkynyl esters to efficiently access pyrazine-1(2 H )-one scaffolds. This organo-catalyzed [5 + 1] annulation features a broad substrate scope concerning both annulating partners. Total syntheses of peramine and formal syntheses of dibromophakellin natural products were achieved to show the application potential of the method.
Databáze:	MEDLINE
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