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

Kripalaya Ratheesh Arya; Hazel A. Sparkes; Karnam Jayaram Pillai Rajendra Prasad

doi:10.1007/s12039-018-1428-1

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

Kripalaya Ratheesh Arya, Hazel A. Sparkes, Karnam Jayaram Pillai Rajendra Prasad^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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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 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.

Original language	English
Article number	41
Number of pages	12
Journal	Journal of Chemical Sciences
Volume	130
Issue number	4
Early online date	28 Mar 2018
DOIs	https://doi.org/10.1007/s12039-018-1428-1
Publication status	Published - 1 Apr 2018

Keywords

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

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title = "An efficient one-pot synthesis of carbazole fused benzoquinolines and pyridocarbazoles",

abstract = "A one-pot, solvent-free protocol for the synthesis of chloro-substituted benzoquinoline-carbazole derivatives via a modified Friedl{\"a}nder hetero-annulation reaction between 2, 3, 4, 9-tetrahydrocarbazol-1-one and 3-amino-2-naphthoic acid in the presence of 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 Friedl{\"a}nder 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 = "benzoquinoline-carbazoles, carbazole substituted pyridocarbazole, Modified Friedl{\"a}nder reaction, pseudo multicomponent reaction",

author = "Arya, {Kripalaya Ratheesh} and Sparkes, {Hazel A.} and Prasad, {Karnam Jayaram Pillai Rajendra}",

year = "2018",

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doi = "10.1007/s12039-018-1428-1",

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journal = "Journal of Chemical Sciences ",

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TY - JOUR

T1 - An efficient one-pot synthesis of carbazole fused benzoquinolines and pyridocarbazoles

AU - Arya, Kripalaya Ratheesh

AU - Sparkes, Hazel A.

AU - Prasad, Karnam Jayaram Pillai Rajendra

PY - 2018/4/1

Y1 - 2018/4/1

N2 - 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 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.

AB - 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 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.

KW - benzoquinoline-carbazoles

KW - carbazole substituted pyridocarbazole

KW - Modified Friedländer reaction

KW - pseudo multicomponent reaction

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JO - Journal of Chemical Sciences

JF - Journal of Chemical Sciences

IS - 4

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ER -

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

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