Mn(OAc) 3 -Mediated One-Pot Condensation-Oxidative Annulation of 2-Alkynylanilines and 1,3-Ketoesters: Synthesis of 2-Substituted Quinolines.

Autor: Punjajom K; Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand., Ruengsangtongkul S; Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand., Tummatorn J; Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.; Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand., Paiboonsombat P; Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand., Ruchirawat S; Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.; Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand., Thongsornkleeb C; Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.; Program on Chemical Biology, Chulabhorn Graduate Institute, Center of Excellence on Environmental Health and Toxicology (EHT), Ministry of Education, 54 Kamphaeng Phet 6, Laksi, Bangkok 10210, Thailand.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Jun 02; Vol. 88 (11), pp. 6736-6749. Date of Electronic Publication: 2023 May 04.
DOI: 10.1021/acs.joc.3c00027
Abstrakt: A general protocol for oxidative annulation was developed for the preparation of 2-methyl-3,4-diacylquinolines directly from 2-alkynylanilines and 1,3-ketoesters. The reactions were mediated by Mn(OAc) 3 in acetic acid at room temperature, which led to the desired quinoline products in one-pot in low to good overall yields on a wide range of substrates. The current method was convenient to conduct and proceeded under mild conditions in short reaction times.
Databáze: MEDLINE
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