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A Visible-Light-Triggered & Rhodamine-B Catalyzed Eco-friendly Synthesis of Benzopyrano[2,3-c]pyrazoles

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Abstract

A one-pot, two-step route is proposed for the synthesis of Benzopyrano[2,3-c]pyrazoles by using salicylaldehydes (1), malononitrile (2) and phenyl hydrazines (3) as substrates and Rhodamine-B as an organophotoredox catalyst in acetonitrile under 23 W CFL irradiation as a source of visible light. Rhodamine- B is a basic red xanthene dye which is extremely water soluble. The utilization of an efficacious, environmentally benign, cost effective and feasible methodology to form C–O and C–N bond via generation of several free radicals after that intramolecular cyclization, are the distinctive traits of this procedure. In addition to this, some other aspects like short reaction time, greener approach and adaptability towards a broad array of substrates, with good to excellent yield of the product further augment the synthesis.

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Acknowledgements

The authors are thankful to SAIF, Punjab University, Chandigarh, India for providing spectral data. Prof. Jagdamba Singh acknowledges the financial support from UGC, New Delhi in the form of BSR Faculty Fellowship (No. F.18-1/2011 (BSR))

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Authors and Affiliations

  1. Department of Chemistry, MKR Government Degree College, Saddique Nagar, Nandgram, Ghaziabad, Uttar Pradesh, India

    Anu Mishra

  2. Environmentally Benign Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad, 211002, India

    Anjali Jaiswal, Yogesh Kumar Pandey & Jagdamba Singh

  3. Department of Chemistry, K.N. Government PG College, Gyanpur, Bhadohi, Uttar Pradesh, India

    Amit Kumar Sharma

  4. Department of Chemistry, LRPG College, Sahibabad, Ghaziabad, Uttar Pradesh, India

    Jaya Singh

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  1. Anu Mishra
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  2. Anjali Jaiswal
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  3. Amit Kumar Sharma
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  5. Jaya Singh
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Correspondence to Jagdamba Singh.

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Mishra, A., Jaiswal, A., Sharma, A.K. et al. A Visible-Light-Triggered & Rhodamine-B Catalyzed Eco-friendly Synthesis of Benzopyrano[2,3-c]pyrazoles. Catal Lett 153, 3795–3804 (2023). https://doi.org/10.1007/s10562-023-04279-1

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  • DOI: https://doi.org/10.1007/s10562-023-04279-1

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