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Photo-reorganization of 3-alkoxy-6-chloro-2-(benzo[b]thiophen-2-yl)-4H-chromen-4-ones: a green and convenient synthesis of angular pentacyclics

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Abstract

Photo-reorganization of 3-alkoxy-6-chloro-2-(benzo[b]thiophen-2-yl)-4H-chromen-4-ones in methanol with Pyrex filtered UV-light from a medium pressure 125 W Hg-vapor lamp led to the formation of angular pentacyclic compounds (dihydro and aromatic products) along with some rearranged chromenones where the product(s) distribution depended upon the structure of 3-alkoxy groups (methoxy, ethoxy, allyloxy and benzyloxy). The phenyl moiety in the 3-benzyloxy group had a profound effect on the dihydro product(s) formation as the latter was in high yield when the alkoxy group was benzyloxy followed by allyloxy, ethoxy and methoxy groups. The present photochemical study represents a general method for the synthesis of some angular pentacyclic – benzothiophene fused xanthenone derivatives in a single step without using any specific and toxic reagent. The structures of the new organic scaffolds obtained were established by their spectral data (UV, IR and NMR).

Graphical abstract: Photo-reorganization of 3-alkoxy-6-chloro-2-(benzo[b]thiophen-2-yl)-4H-chromen-4-ones: a green and convenient synthesis of angular pentacyclics

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Publication details

The article was received on 28 Dec 2016, accepted on 17 Feb 2017 and first published on 17 Feb 2017


Article type: Paper
DOI: 10.1039/C6PP00476H
Citation: Photochem. Photobiol. Sci., 2017, Advance Article
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    Photo-reorganization of 3-alkoxy-6-chloro-2-(benzo[b]thiophen-2-yl)-4H-chromen-4-ones: a green and convenient synthesis of angular pentacyclics

    A. Dalal, R. Khanna, P. Kumar and R. C. Kamboj, Photochem. Photobiol. Sci., 2017, Advance Article , DOI: 10.1039/C6PP00476H

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