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Microwave-assisted Iodine-catalyzed Rapid Synthesis of 6H-indolo[2,3-b] quinolines: Formal Synthesis of Cryptotackieine

[ Vol. 4 , Issue. 3 ]

Author(s):

Prakash T. Parvatkar, Perunninakulath S. Parameswaran, Debasish Bandyopadhyay, Sanghamitra Mukherjee and Bimal K. Banik*   Pages 238 - 241 ( 4 )

Abstract:


Background: Indoloquinoline alkaloids are of great importance due to their unique structure and various biological activities. Several methods have been developed to synthesize indoloquinolines and among those, one-pot methods are of particular importance due to its simplified reaction procedure.

Methods: We investigated the one-pot reaction of indole-3-carboxyaldehyde and aniline in presence of catalytic amount of I2 in automated microwave.

Results: An efficient microwave-mediated tandem synthesis of several linear indoloquinoline alkaloids using 10 mol% iodine as catalyst under mild reaction conditions is described. The reaction involved key steps of imination / nucleophilic addition / annulation / aromatization, all in one pot, in a highly efficient manner under microwave irradiation.

Conclusion: We have developed an extremely rapid and convenient microwave-assisted method for the synthesis of important class of indoloquinolines using environmentally benign I2 as catalyst in one-pot.

Keywords:

Cryptotackieine, indoloquinoline, iodine, microwave, tandem.

Affiliation:

Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, CSIR-National Institute of Oceanography, Regional Centre, Kochi 682 018, Department of Chemistry, The University of Texas-Pan American, Edinburg, TX 78539, Department of Chemistry, The University of Texas-Pan American, Edinburg, TX 78539, Community Health System of South Texas, 3135 South Sugar Road, Edinburg, TX 78539

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