α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-]quinoxalines, quinazolinones, and other N-heterocycles decarboxylative oxidative annulation reaction

• Published in: RSC advances Vol. 1; no. 61; pp. 3722 - 3728
• Main Authors: Viji, Mayavan, Vishwanath, Manjunatha, Sim, Jaeuk, Park, Yunjeong, Jung, Chanhyun, Lee, Seohu, Lee, Heesoon, Lee, Kiho, Jung, Jae-Kyung
• Format: Journal Article
• Language: English
• Published: 07-10-2020
• ISSN: 2046-2069
• DOI: 10.1039/d0ra07093a

A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-
a
]quinoxalines, quinazolinones, and indolo[1,2-
a
]quinoxaline has been developed. The key features of our method include the
in situ
generation of aldehyde from α-hydroxy acid in the presence of TBHP (
tert
-butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields.
A TBHP mediated, metal-free approach for the synthesis of quinoxalines, quinazolinones, and indolo quinoxaline was developed from alpha hydroxy acids
via
decarboxylation followed by condensation.