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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 chrome-nones 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).

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Authors and Affiliations

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

    Aarti Dalai, Radhika Khanna, Parvin Kumar & Ramesh C. Kamboj

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  1. Aarti Dalai
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  2. Radhika Khanna
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  4. Ramesh C. Kamboj
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Correspondence to Ramesh C. Kamboj.

Additional information

CCDC 1516032. For crystallographic data in CIF. or other electronic format see DOI: 10.1039/c6pp00476h

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Dalai, A., Khanna, R., Kumar, P. et al. 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. Photochem Photobiol Sci 16, 672–682 (2017). https://doi.org/10.1039/c6pp00476h

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  • DOI: https://doi.org/10.1039/c6pp00476h

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