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Synthesis 1995; 1995(3): 276-284
DOI: 10.1055/s-1995-3893
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A New Approach to the Synthesis of N-Protected 2- and 5-Substituted 3-Halopyrroles

Thierry Masquelin, Daniel Obrecht*
  • *Pharma Research, F. Hoffmann-La Roche AG, CH-4002 Basel, Switzerland
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Publication Date:
31 December 2000 (online)

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A new and efficient method for the preparation of N-protected 5- and 2-substituted 3-bromopyrroles 15 and 16 via acid-catalyzed cyclization of the corresponding acetylenic ketones 6 and acetylenic acetals 14 has been found (Scheme 3). Using this methodology, rapid and quite general access to highly substituted pyrroles, which are known to exhibit a number of interesting biological activities, has been established.

acetylenic ketones - acetylenic acetals - acid-catalyzed cyclization - 2-substituted 3-bromopyrroles - 5-substituted 3-bromopyrroles