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Synthesis 2012(3): 409-416
DOI: 10.1055/s-0031-1289656
DOI: 10.1055/s-0031-1289656
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthetic Approaches to Highly Functional β-Carboline Building Blocks via Allylic Amidation
Further Information
Publication History
Received
7 November 2011
Publication Date:
22 December 2011 (online)


Abstract
A new, straightforward synthesis of highly functional β-carboline building blocks is presented that makes use of allylic amidation methodology. The products obtained carry a terminal double bond as well as an easy-to-deprotect amide, which make them perfectly suitable for further functionalization. The use of the trifluoroacetamide group is exploited in a dual fashion; it acts as a protecting group and functions as the nucleophile for the allylic amidation reaction.
Key words
indoles - β-carbolines - allylic amidation - heterocycles - Stille reaction
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