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Synthesis 2007(10): 1559-1565  
DOI: 10.1055/s-2007-966041
PAPER
© Georg Thieme Verlag Stuttgart · New York

Novel Synthesis of Arylethynyl Heterocycles

Roger Soleya, Fernando Albericioa,b, Mercedes Álvarez*a,c
a Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, 08028 Barcelona, Spain
b Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain
c Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028 Barcelona, Spain
e-Mail: malvarez@pcb.ub.es;
Further Information

Publication History

Received 14 February 2007
Publication Date:
02 May 2007 (online)

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Abstract

A new and simple synthesis of 2-arylethynylindole and 2-arylethynylpyrrole is described. N-Deprotection and subsequent base-catalyzed elimination of N-tosylheteroaryl benzyl ketones are the key steps of the process.

Key words

acetylenes - indole - pyrrole - elimination - tosyl protecting group

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9

Reverse phase analytical HPLC was performed on a Waters Alliance 2695 separation module using a Waters Xterra MS C18 column (150 × 4.6 mm, 5 µm) and a Waters 996 PDA detector at 254 nm. The solvent system used was: A: TFA-H2O, 0.045%, B: TFA-MeCN, 0.036%. A linear gradient from 50% B to 100% B over 15 minutes was used. The retention times of 1 and 3 were 9.1 and 8.4 min, respectively.