Base promoted coupling of α-ketoacids and 2-substituted aromatic amines: Green synthesis of diverse benzoxazoles, benzothiazoles, quinoxalinones and benzoxazinones and its practical application.

Autor: Mathavan, Sivagami, Ramesh, Subburethinam, Yamajala, Rajesh B. R. D.
Předmět:
Zdroj: Synthetic Communications; 2024, Vol. 54 Issue 1, p50-65, 16p
Abstrakt: Synthesis of 2-aryl substituted benzoxazoles, benzothiazoles, and quinoxalinones via decarboxylative coupling of α-keto acids with 2-aminophenol, 2-aminothiophenol, and OPD (o-phenylenediamine), using K2CO3 as a base in water at room temperature, and as well as solvent-free grinding and the synthesis of benzoxazinones from the reaction of α-keto acids with 2-aminophenol at 60 °C have been reported. Both the protocols afforded a wide range of desired products with excellent functional group tolerance in yields of 87-99%. The major advantages of these approaches are catalyst-free protocol, short reaction times, straightforward workup, and chromatographyfree processing of the products. Additionally, to test the translational demand of this methodology, the synthesis of 2-(3,5-dichlorophenyl)- 6-methylbenzo[d]oxazole was carried out which is a key structure of tafamidis, a commercially available drug. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index