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Pot-economic synthesis of diarylpyrazoles and pyrimidines involving Pd-catalyzed cross-coupling of 3-trifloxychromone and triarylbismuth

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Abstract

The present study reveals the formation of 3,4-diarylpyrazole and 4,5-diarylpyrimidine in one-pot operation starting from 3-trifloxychromone and triarylbismuth. The complete process encompasses two steps in the one-pot operation. The first step leads to the formation of isoflavone via cross-coupling reaction of 3-trifloxychromone and triarylbismuth as a threefold arylating reagent. These isoflavones were further converted into 3,4-diarylpyrazole and 4,5-diarylpyrimidine using hydrazine hydrate and guanidinium chloride in the successive step in the same pot. Interestingly the formation of 3,4-diarylpyrazole was achieved in the shortest reaction time i.e., 30 min that too at room temperature. Overall the developed methodology provides easy access to the medicinally important diarylpyrazole and pyrimidine moiety in one-pot operation and in short reaction time.

Graphical Abstract

Synopsis The work presented here describes the novel methodology for the formation of medicinally important heterocycles 3,4-diarylpyrazole and 4,5-diarylpyrimidine in one-pot operation starting from 3-trifloxychromone and triarylbismuth.

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Acknowledgements

We acknowledge the financial support (No. 02(0091)/12/EMR-II) received from the Council of Scientific and Industrial Research (CSIR), New Delhi for this work. A.K. sincerely acknowledges the support of Scientific and Industrial Research (CSIR), New Delhi for fellowships and also thanks IIT Kanpur for providing financial assistance and infrastructure. He sincerely acknowledges the support for Mahatma Gandhi Central University for providing all other support.

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Authors and Affiliations

  1. Department of Chemistry, School of Physical and Material Sciences, Mahatma Gandhi Central University, Motihari, Bihar, 845 401, India

    Abhijeet Kumar

  2. Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, Uttar Pradesh, 208 016, India

    Abhijeet Kumar & Maddali L N Rao

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  1. Abhijeet Kumar
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Correspondence to Abhijeet Kumar.

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Kumar, A., Rao, M.L.N. Pot-economic synthesis of diarylpyrazoles and pyrimidines involving Pd-catalyzed cross-coupling of 3-trifloxychromone and triarylbismuth. J Chem Sci 130, 165 (2018). https://doi.org/10.1007/s12039-018-1565-6

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