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Visible Light Mediated Organophotoredox-Catalyzed One-Pot Domino Synthesis of Novel 6,7 Disubstituted 1H-Pyrroles

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Abstract

The development of environmentally benign protocols to synthesize novel N-heterocycles is vital in the field of synthetic organic chemistry. We herein report a successful one-pot domino synthesis of novel 6,7 disubstituted 1H-pyrroles using substituted phenacyl bromide, barbituric acid/Meldrums acid, aromatic amines catalysed by 5 mol% Fluorescein in presence of visible light. This procedure is a useful and adaptable method for the synthesis of pyrroles since it is compatible with a wide range of sensitive functional groups, does not require column chromatography purification. During the reaction, Fluorescein may catalyse the formation of enamine leading to amino alcohol which subsequently undergoes dehydration to give 6,7 disubstituted 1H-pyrroles. All the synthesized derivatives were obtained in 90–95% yields and were characterized by 1H, 13C NMR and HRMS (ESI) analysis.

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Acknowledgements

The authors thank SIF, IISc Bangalore for spectral analysis.

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The author(s) received no financial support for the research, authorship, and/or publication of this article.

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  1. Department of Sciences and Humanities, School of Engineering and Technology, CHRIST (Deemed To Be University), Kumbalagodu, Mysore Road, Bengaluru, 560074, India

    Santhosh Govindaraju

  2. Department of Chemistry, Surana College, South End Road, Basavanagudi, Bengaluru, 560004, India

    Sumaiya Tabassum

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  1. Santhosh Govindaraju
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Govindaraju, S., Tabassum, S. Visible Light Mediated Organophotoredox-Catalyzed One-Pot Domino Synthesis of Novel 6,7 Disubstituted 1H-Pyrroles. Top Catal (2022). https://doi.org/10.1007/s11244-022-01580-y

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