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Asian Journal of Research in Chemistry
Year : 2018, Volume : 11, Issue : 2
First page : ( 337) Last page : ( 343)
Print ISSN : 0974-4169. Online ISSN : 0974-4150.
Article DOI : 10.5958/0974-4150.2018.00061.5

Nitration of C13, C18 and C23 Carbazole Alkaloids using Ceric Ammonium Nitrate (CAN)

Chakraborty Mumu*

Department of Chemistry, Govt. Girls’ General Degree College, 7, Mayur Bhanj Road, Kolkata-700023, West Bengal, India

*Corresponding Author E-mail: mumu_chak@yahoo.com

Online published on 2 June, 2018.

Abstract

In course of our study on the nitration of carbazole alkaloids isolated from Murraya koenigii, we have observed that there is no report of the nitration of pyranocarbazole alkaloids with ceric ammonium nitrate in the literature. So we were interested to study the nitration of pyranocarbazole alkaloids girinimbine, koenidine, koenimbine and mahanimbine isolated from M. koenigii. Interestingly selective mononitation occurred in girinimbine and koenidine, whereas koenimbine and mahanimbine afforded dinitro derivatives as major products. Nitration of glycozolidine with ceric ammonium nitrate on the other hand furnished a dimeric diniro compound. The mechanism of formation of new nitro pyranocarbazole alkaloids in these reactions will be discussed.

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Keywords

Murraya koenigii, alkaloids, pyranocarbazole, nitration, ceric ammonium nitrate.

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