Flow synthesis of annulated 5-aryl-substituted pyridines by tandem intramolecular inverse-electron-demand hetero-/retro-DielsaAlder reaction

5-Aryl-substituted annulated pyridines can be accessed directly from the corresponding acetylene substituted pyrimidines through an intramolecular inverse-electron-demand hetero-/retro-DielsaAlder (ihDA/rDA) reaction cascade carried out in continuous flow. Exploiting this new process, a series of cy...

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Bibliographic Details
Published in:Tetrahedron letters 2013-12, Vol.54 (49), p.6703-6707
Main Authors: Martin, Rainer, Lenz, Mario, Alzieu, Thibaut, Aebi, Johannes, zy, Liliane
Format: Article
Language:English
Subjects:
Acetylene
Boiling
Chlorobenzenes
Pyridines
Pyrimidines
Solvents
Tetrahedrons
Toluene
Online Access:Get full text
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Summary:5-Aryl-substituted annulated pyridines can be accessed directly from the corresponding acetylene substituted pyrimidines through an intramolecular inverse-electron-demand hetero-/retro-DielsaAlder (ihDA/rDA) reaction cascade carried out in continuous flow. Exploiting this new process, a series of cycloalka[c]pyridines that represent useful building blocks for medicinal chemistry were prepared in good to excellent yields with short processing times (
ISSN:0040-4039
DOI:10.1016/j.tetlet.2013.09.069