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Issue 3, 2014
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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

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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.

Graphical abstract: 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

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Publication details

The article was received on 20 Nov 2013, accepted on 20 Dec 2013 and first published on 07 Jan 2014


Article type: Communication
DOI: 10.1039/C3PP50396H
Photochem. Photobiol. Sci., 2014,13, 488-491

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    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

    P. Jindal, R. Bhatia, S. Khullar, S. K. Mandal and R. C. Kamboj, Photochem. Photobiol. Sci., 2014, 13, 488
    DOI: 10.1039/C3PP50396H

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