Practical synthesis of 3-(2-arylethylidene)isoindolin-1-ones (analogues of AKS-182) and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones

Autor:	Angel Palillero-Cisneros, Joel Luis Terán-Vázquez, Mario Ordóñez, Victoria Labastida-Galván
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Double bond Isobenzofuran 010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound Computational chemistry Drug Discovery Selectivity Acetonitrile Isomerization
Zdroj:	Tetrahedron. 76:130838
ISSN:	0040-4020
Popis:	A simple and practical method is reported for the synthesis of 3-(2-arylethylidene)isoindolin-1-ones and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones, proceeding with good to excellent yields and (E:Z) selectivity. This methodology involves the sequential reduction-dehydration reaction of readily obtained 3-(2-oxo-2-arylethyl)isoindolin-1-ones and 3-(2-oxo-2-arylethyl)isobenzofuran-1(3H)-ones followed by a base-catalyzed double bond isomerization with K2CO3 in acetonitrile. The development of a concise synthesis of AKS-182 has been achieved using this methodology.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7312dc2f9a4bbac715e303cdc6697aa8 https://doi.org/10.1016/j.tet.2019.130838 Zobrazit plný text záznamu Full Text from ScienceDirect