Pd(0)-Catalyzed Intramolecular Heck reaction of 2/3-Aryl(amino)methyl-3/2-bromoindoles: Syntheses of 3,4-Benzo[c]-β-carbolines, Benzo[4,5]isothiazolo[2,3-a]indole 5,5-Dioxides, and 1,2-Benzo[a]-γ-carbolines

Autor:	Velu Saravanan, Potharaju Raju, Arasambattu K. Mohanakrishnan, Vinayagam Pavunkumar
Rok vydání:	2021
Předmět:	Indole test Sulfonyl chemistry.chemical_classification chemistry.chemical_compound chemistry Heck reaction Intramolecular force Aryl Organic Chemistry Aromatization Protecting group Mesitylene Medicinal chemistry
Zdroj:	The Journal of Organic Chemistry. 86:1925-1937
ISSN:	1520-6904 0022-3263
Popis:	One-pot synthesis of 3,4-benzo[c]-β-carbolines was achieved from 2-aryl(tosylamino)methyl-3-bromoindoles via 10 mol % Pd(OAc)2/PPh3-mediated intramolecular Heck coupling using K2CO3 as a base in DMF at 110 °C with concomitant aromatization through an elimination of tosylsulfinic acid. Under identical conditions, the isomeric 3-aryl(tosylamino)methyl-2-bromoindoles upon intramolecular Heck reaction furnished benzo[4,5]isothiazolo[2,3-a]indole 5,5-dioxides instead of the expected γ-carbolines. However, synthesis of the expected γ-carboline framework, 3-tosyl-6,9-dihydro-1,2-benzo[a]-γ-carbolines, could be achieved from 3-aryl(tosylamino)methyl-2-bromoindoles containing a mesitylene sulfonyl unit as a protecting group on the indole nitrogen.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::acb209e7aa6864922fe2575cea765a9a https://doi.org/10.1021/acs.joc.0c02152 Zobrazit plný text záznamu