Copper(II)-Mediated ortho-Selective C(sp2)–H Tandem Alkynylation/Annulation and ortho-Hydroxylation of Anilides with 2-Aminophenyl-1H-pyrazole as a Directing Group

Autor:	Wei Wang, Jie Jack Li, Wan-Chen Cindy Lee
Rok vydání:	2018
Předmět:	Annulation Organic base Tandem 010405 organic chemistry Organic Chemistry chemistry.chemical_element Pyrazole 010402 general chemistry 01 natural sciences Medicinal chemistry Copper 0104 chemical sciences Hydroxylation chemistry.chemical_compound Alkynylation chemistry Group (periodic table)
Zdroj:	The Journal of Organic Chemistry. 83:2382-2388
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.7b02893
Popis:	2-Aminophenyl-1H-pyrazole has been identified as a viable directing group to promote copper(II)-mediated ortho-selective sp2 C–H bond tandem alkynylation/annulation of anilides with terminal alkynes to offer arylmethylene isoindolinones. Meanwhile, copper(II)-mediated ortho-selective sp2 C–H hydroxylation of anilides has also been optimized as the major reaction pathway by using Cu(OAc)2 as the promoter and 1,1,3,3-tetramethylguanidine as an organic base. Recovery of the directing group was achieved by hydrazinolysis for arylmethylene isoindolinones and basic hydrolysis for the hydroxylation products.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b0e9dd9f8ce995bb77ff1f196ac1021e https://doi.org/10.1021/acs.joc.7b02893 Zobrazit plný text záznamu