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

  • Kripalaya Ratheesh Arya
  • Hazel A Sparkes
  • Karnam Jayaram Pillai Rajendra Prasad
Regular Article
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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.

Keywords

Modified Friedländer reaction benzoquinoline-carbazoles pseudo multicomponent reaction carbazole substituted pyridocarbazole 

Notes

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.

Supplementary material

12039_2018_1428_MOESM1_ESM.pdf (2.3 mb)
Supplementary material 1 (pdf 2319 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  • Kripalaya Ratheesh Arya
    • 1
  • Hazel A Sparkes
    • 2
  • Karnam Jayaram Pillai Rajendra Prasad
    • 1
  1. 1.Department of ChemistryBharathiar UniversityCoimbatoreIndia
  2. 2.School of ChemistryUniversity of BristolBristolUK

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