4.7 Article

Cycloaromatization Approach to Polysubstituted Indolizines from 2-Acetylpyrroles: Decoration of the Pyridine Unit

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 3, Pages 1283-1288

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo302590a

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Funding

  1. National Research Foundation of Korea (NRF)
  2. Ministry of Education, Science and Technology [2012M3A7B4049656]
  3. National Research Foundation of Korea [2012M3A7B4049656] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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A new synthetic route to indolizines with various substituents on the pyridine moiety was developed by utilizing a facile cycloaromatization of 2-acetylpyrrole derivatives. Without isolation, the resulting intermediates were allowed to react with various electrophiles to afford a range of indolizines. In particular, Suzuki-Miyaura cross-coupling of O-triflates with (hetero)arylboronic acids permitted introduction of diverse substituents at the C8 position of an indolizine skeleton.

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