通过（E）-3-芳基乙烯基-4H-色烯-4-酮的光诱导重排合成苯甲酰基-5-（2-羟基苯基）甲酮。

Synthesis of Benzoaryl-5-yl(2-hydroxyphenyl)methanones via Photoinduced Rearrangement of (E)-3-Arylvinyl-4H-chromen-4-ones.

机构信息

Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University , Xi'an 710119, People's Republic of China.

出版信息

Org Lett. 2017 Nov 3;19(21):5984-5987. doi: 10.1021/acs.orglett.7b03007.

DOI:10.1021/acs.orglett.7b03007

PMID:29047271

Abstract

A concise and efficient photoinduced rearrangement of (E)-3-arylvinyl-4H-chromen-4-ones for the synthesis of benzoaryl-5-yl(2-hydroxyphenyl)methanones is described. Benzoaryl-5-yl-(2-hydroxyphenyl)methanones were obtained in 77-95% yields via the irradiation of (E)-3-arylvinyl-chromones in the 95% EtOH with a high-pressure mercury lamp at room temperature under Ar atmosphere. The reported method provides a novel procedure for the synthesis of α,α'-diaryl ketone derivatives without addition of any transition metals and oxidants or other additives. A plausible mechanism was proposed, and the rearrangement product was characterized by NMR, HRMS, and X-ray.

摘要

描述了一种简洁高效的（E）-3-芳基乙烯基-4H-色烯-4-酮的光诱导重排反应，用于合成苯并芳基-5-基（2-羟基苯基）甲酮。通过在室温下在氩气氛下用高压汞灯照射（E）-3-芳基乙烯基-色酮在 95%乙醇中，以 77-95%的收率得到苯并芳基-5-基（2-羟基苯基）甲酮。该报道的方法提供了一种无需添加任何过渡金属和氧化剂或其他添加剂即可合成α，α'-二芳基酮衍生物的新方法。提出了一种合理的机制，并通过 NMR、HRMS 和 X 射线对重排产物进行了表征。