Visible-Light 2,4-Dinitrophenol-Mediated Photoannulation of α-Azidochalcones into 2,5-Diaryloxazoles.

Autor: Newar UD; Applied Organic Chemistry Group, Chemical Sciences & Technology Division, CSIR-North East Institute of Science & Technology (NEIST), Jorhat 785006, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Borra S; Applied Organic Chemistry Group, Chemical Sciences & Technology Division, CSIR-North East Institute of Science & Technology (NEIST), Jorhat 785006, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Maurya RA; Applied Organic Chemistry Group, Chemical Sciences & Technology Division, CSIR-North East Institute of Science & Technology (NEIST), Jorhat 785006, India.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2022 Jun 24; Vol. 24 (24), pp. 4454-4458. Date of Electronic Publication: 2022 Jun 14.
DOI: 10.1021/acs.orglett.2c01691
Abstrakt: A novel and efficient visible-light 2,4-dinitrophenol (2,4-DNP) mediated photoannulation of α-azidochalcones into 2,5-diaryloxazoles was developed. The carbon-carbon double bond of α-azidochalcone was cleaved, leading to the formation of new C-O and C-N bonds in the photoannulation. Control experiments were carried out, and a plausible mechanism of the photoannulation was proposed. The scope of the reaction was studied by synthesizing a series of 2,5-diaryloxazoles including two naturally occurring oxazoles (Texamine and Balsoxin) in excellent yields.
Databáze: MEDLINE