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由3-丙炔氧基色原酮一步光化学合成5-(噻吩-3-基)吡喃并[2,3-c]色烯-2(3H)-酮:分子内Paterno-Buchi反应一例

One-shot photochemical synthesis of 5-(thiophen-3-yl)pyrano[2,3-c]chromen-2(3H)-ones from 3-propynyloxy-chromenones: a case of an intramolecular Paterno-Buchi reaction.

作者信息

Jindal Pooja, Bhatia Rimpy, Khullar Sadhika, Mandal Sanjay K, Kamboj Ramesh C

机构信息

Department of Chemistry, Kurukshetra University, Kurukshetra-136119, Haryana, India.

出版信息

Photochem Photobiol Sci. 2014 Mar;13(3):488-91. doi: 10.1039/c3pp50396h. Epub 2014 Jan 29.

DOI:10.1039/c3pp50396h
PMID:24473453
Abstract

5-(Thiophen-3-yl)pyrano[2,3-c]chromen-2(3H)-ones (2), angular tricyclic compounds, were synthesized in significantly high yields through the photoinduced intramolecular coupling of the acetylenic group with the carbonyl centre in 3-(prop-2-ynyloxy)-2-(thiophen-3-yl)-4H-chromen-4-ones (1). This photoreaction is a case of an intramolecular Paterno-Buchi reaction and is unprecedented in 3-propynyloxy-chromenones. The structure of 2 has been determined by spectroscopic (FTIR, NMR and mass) and single crystal X-ray crystallographic studies.

摘要

5-(噻吩-3-基)吡喃并[2,3-c]色烯-2(3H)-酮(2),即角型三环化合物,通过3-(丙-2-炔氧基)-2-(噻吩-3-基)-4H-色烯-4-酮(1)中炔基与羰基中心的光诱导分子内偶联反应,以相当高的产率合成。该光反应是分子内Paterno-Buchi反应的一个实例,在3-丙炔氧基色烯酮中是前所未有的。2的结构已通过光谱(FTIR、NMR和质谱)和单晶X射线晶体学研究确定。

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