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An efficient one-pot synthesis of carbazole fused benzoquinolines and pyridocarbazoles

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Abstract

A one-pot, solvent-free protocol for the synthesis of chloro-substituted benzoquinoline-carbazole derivatives via a modified Friedländer hetero-annulation reaction between 2, 3, 4, 9-tetrahydrocarbazol-1-one and 3-amino-2-naphthoic acid in the presence of \(\hbox {POCl}_{3}\) is described. In addition, the direct pseudo multicomponent transformation of 2, 3, 4, 9-tetrahydrocarbazol-1-one, malononitrile and 9-ethyl-3-carbazolecarboxaldehyde results in the formation of a multifunctionalized carbazole through a Knoevenagel–Michael addition-cyclization reaction has also been reported. All the newly synthesized molecules were deduced by spectral and analytical methods.

Graphical Abstract

A modified Friedländer hetero-annulation reaction between 2, 3, 4, 9-tetrahydro-1H-carbazol-1-one and 3-amino-2-naphthoic acid under solvent-free condition afforded chloro-substituted benzoquinoline-carbazole derivatives. In addition, the direct pseudo multicomponent transformation of 2, 3, 4, 9-tetrahydro-1H-carbazol-1-one, malononitrile and 9-ethyl-3-carbazolecarboxaldehyde results in the formation of dimerised carbazoles.

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Acknowledgements

We would like to thank the University of Mysore, for NMR data. X-ray diffraction was funded by University of Bristol, United Kingdom. Financial support from “UGC-Emeritus fellowship” [Award NO.F.6-6/2015-17/EMERITUS-2015-17-OBC-7410/ (SAII)] for research, is gratefully acknowledged by Prof. K. J. Rajendra Prasad. Arya. K. R acknowledges the award of BSR-Senior Research Fellowship by University Grant Commission (UGC), New Delhi.

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Authors and Affiliations

  1. Department of Chemistry, Bharathiar University, Coimbatore, Tamilnadu, 641 046, India

    Kripalaya Ratheesh Arya & Karnam Jayaram Pillai Rajendra Prasad

  2. School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK

    Hazel A Sparkes

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  1. Kripalaya Ratheesh Arya
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Correspondence to Karnam Jayaram Pillai Rajendra Prasad.

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Arya, K.R., Sparkes, H.A. & Prasad, K.J.P.R. An efficient one-pot synthesis of carbazole fused benzoquinolines and pyridocarbazoles. J Chem Sci 130, 41 (2018). https://doi.org/10.1007/s12039-018-1428-1

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