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Synthesis 2012(5): 747-754  
DOI: 10.1055/s-0031-1289675
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Microwave-Assisted Synthesis of 1,3-Disubstituted β-Carbolines from α-(Alkylideneamino)nitriles and Gramine

Julien Letessiera, Heiner Deterta, Katharina Götzb, Till Opatz*a
a Institute for Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Fax: +49(6131)3922338; e-Mail: opatz@uni-mainz.de;
b Institute for Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
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Publikationsverlauf

Received 28 November 2011
Publikationsdatum:
23. Januar 2012 (online)

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Abstract

Reaction of deprotonated α-(alkylidenamino)nitriles with gramine in the presence of tributylphosphine furnishes α-substituted imines of tryptophane nitrile. Their subsequent intramolecular cyclization followed by dehydrocyanation and oxidation affords 1,3-disubstituted β-carbolines.

Key words

imines - α-aminonitriles - cyclization - alkaloids - β-carbolines

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CCDC-847261 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.