Issue 10, 2014
From the journal:

RSC Advances

C–N bond formation via Cu-catalyzed cross-coupling with boronic acids leading to methyl carbazole-3-carboxylate: synthesis of carbazole alkaloids†‡

Sk. Rasheed,ab   D. Nageswar Rao,ab   K. Ranjith Reddy,ab   S. Aravinda,b   Ram A. Vishwakarmab  and  Parthasarathi Das*ab  

* Corresponding authors

a Academy of Scientific and Innovative Research (AcSIR), India

b Medicinal Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu-180001, India
E-mail: partha@iiim.ac.in
Fax: +91-191-2569019

Abstract

Copper promoted N-arylation of methyl 4-amino-3-iodobenzoate with boronic acids followed by Pd-catalyzed intramolecular C–H arylation provides an efficient route to methyl carbazole-3-carboxylate derivatives. This methodology was implemented in the synthesis of naturally occurring carbazole alkaloids clausine C, clausine H, clausine L, clausenalene, glycozoline, glycozolidine, glycozolidal and sansoakamine.

Graphical abstract: C–N bond formation via Cu-catalyzed cross-coupling with boronic acids leading to methyl carbazole-3-carboxylate: synthesis of carbazole alkaloids

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Article information

DOI
https://doi.org/10.1039/C3RA44903C
Article type
Paper
Submitted
05 Sep 2013
Accepted
22 Oct 2013
First published
23 Oct 2013

RSC Adv., 2014,4, 4960-4969

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C–N bond formation via Cu-catalyzed cross-coupling with boronic acids leading to methyl carbazole-3-carboxylate: synthesis of carbazole alkaloids

Sk. Rasheed, D. N. Rao, K. R. Reddy, S. Aravinda, R. A. Vishwakarma and P. Das, RSC Adv., 2014, 4, 4960 DOI: 10.1039/C3RA44903C

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