Synthesis 2014; 46(07): 893-898
DOI: 10.1055/s-0033-1338591
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot Conversion of 1-Bromo-β-carboline and 1-Bromocarbazole into Pentacyclic­ Compounds by Suzuki Cross-Coupling Followed by Spontaneous Cyclization

André P. Gehring
Department of Pharmacy - Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstr. 5-13, 81377 Munich, Germany   Fax: +49(89)218077802   Email: franz.bracher@cup.uni-muenchen.de
,
Tim Tremmel
Department of Pharmacy - Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstr. 5-13, 81377 Munich, Germany   Fax: +49(89)218077802   Email: franz.bracher@cup.uni-muenchen.de
,
Franz Bracher*
Department of Pharmacy - Center for Drug Research, Ludwig-Maximilians University Munich, Butenandtstr. 5-13, 81377 Munich, Germany   Fax: +49(89)218077802   Email: franz.bracher@cup.uni-muenchen.de
› Author Affiliations
Further Information

Publication History

Received: 07 December 2013

Accepted after revision: 08 January 2014

Publication Date:
10 February 2014 (eFirst)

Abstract

This work describes a straightforward one-pot conversion of 1-bromo-β-carboline and 1-bromocarbazole into pentacyclic compounds. Suzuki cross-coupling with various 2-methoxycarbonylphenylboronic acids was followed by spontaneous lactamization to give the target products. Coupling of 1-bromo-β-carboline with 2-formylphenylboronic acid also gave the oxo product through oxidative cyclization, whereas in the carbazole series, the intermediate hemiaminals undergo a disproportionation reaction to give both the oxo and the methylene product.

 
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