Acid-Catalyzed Condensation of o-Phenylenediammines and o-Aminophenols with α-Oxodithioesters: A Divergent and Regio­selective Synthesis of 2-Methylthio-3-aryl/Heteroarylquinoxalines and 2-Acylbenzoxazoles

Autor:	Kanchugarakoppal S. Rangappa, Toreshettahally R. Swaroop, Kuppalli R Kiran, Seegehally M Anil, Maralinganadoddi P. Sadashiva, Jeegundipattana B Shruthi, Kodipura P. Sukrutha
Rok vydání:	2019
Předmět:	chemistry.chemical_classification 010405 organic chemistry Chemistry Aryl Organic Chemistry Regioselectivity Benzoxazole Sulfonic acid 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Carboxylesterase Aniline Quinoxaline
Zdroj:	Synthesis. 51:4205-4214
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0039-1690616
Popis:	o-Phenylenediammines and o-aminophenols were reacted with α-oxodithioesters in a highly regioselective fashion to give 2-methylthio-3-aryl/heteroarylquinoxalines and 2-acylbenzoxazoles in 55–94% and 45–86%, respectively, in the presence of p-toluene sulfonic acid catalyst. Control experiments involving reaction of aniline with a α-oxodithioester indicated that the thiocarbonyl group is more reactive than the carbonyl group. Based on this, probable mechanisms for the formation of quinoxalines and benzoxazoles are given. Biological targets of the quinoxalines and benzoxazoles were identified by bioinformatics. It was found that quinoxalines have good binding affinity with human dual-specificity tyrosine-phosphorylation-regulated kinase 1A and benzoxazoles with human carboxylesterase.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::11a1865c830bcde32c7858b10ae4606a https://doi.org/10.1055/s-0039-1690616 Zobrazit plný text záznamu