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Intramolecular Diels-Alder reactions of 1,2,4-triazines. Synthesis of 2,3-cyclopentenopyridines and 5,6,7,8-tetrahydroquinolines

โœ Scribed by Taylor, Edward C.; Macor, John E.; French, Larry G.


Book ID
120052874
Publisher
American Chemical Society
Year
1991
Tongue
English
Weight
867 KB
Volume
56
Category
Article
ISSN
0022-3263

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โœ Edward C Taylor; Joseph L Pont ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 166 KB

Inverse electron-demand Diels-Alder reactions of 1,2,4-triazines, where the dienophile is present in a sidechain tethered to the azadiene, can proceed with remarkable facility, leading to a variety of condensed pyridines (Scheme 1). Several recent publications from our laboratory have served to illu

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Syntheses of several 6,6,6-tricyclic condensed pyridines and pyrazines utilizing intramolecular Diels-Alder reactions of 1,2,4-triazines with alkyne and nitrile dienophiles are detailed. The cyclizations are facilitated by the presence 01 conformationally restrictive planar aromatic rings in the cha