Newar Uma Devi, Borra Satheesh, Maurya Ram Awatar
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.
Org Lett. 2022 Jun 24;24(24):4454-4458. doi: 10.1021/acs.orglett.2c01691. Epub 2022 Jun 14.
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.
开发了一种新颖且高效的可见光介导的2,4-二硝基苯酚（2,4-DNP）介导的α-叠氮基查尔酮光环化生成2,5-二芳基恶唑的反应。α-叠氮基查尔酮的碳-碳双键发生断裂，导致在光环化反应中形成新的C-O键和C-N键。进行了对照实验，并提出了一个合理的光环化反应机理。通过合成一系列2,5-二芳基恶唑，包括两种天然存在的恶唑（特沙明和巴尔索辛），以优异的产率研究了该反应的适用范围。
