which employ [5 + 1],2b,3a,4 [2 + 2 + 1 + 1],5 [2 + 2 + 2],6
[3 + 3],7 [4 + 2]8 and [3 + 2 + 1]9 synthetic strategies with
respect to pyridine ring disconnection, each synthesis must be
carefully planned due to the incompatibility of certain functional
groups. Therefore, there is a continuing need to generate new
and improved methods for pyridine synthesis. The [5 + 1]
annulation of 1,5-dicarbonyl compounds and their equivalents
with ammonia represents one of the most simple and reliable
routes due to its straightforward concept.2b,4 However, the
problem associated with this transformation is the availability
of suitable starting materials. Thus, it is of great importance to
explore more appropriate precursors for efficient synthesis of
pyridine derivatives via a [5 + 1] annulation strategy.
Temperature-Controlled Synthesis of Substituted
Pyridine Derivatives via the [5C + 1N]
Annulation of 1,1-Bisalkylthio-1,4-pentanedienes
and Ammonium Acetate
Jianglei Hu, Qian Zhang,* Hongjuan Yuan, and Qun Liu*
Department of Chemistry, Northeast Normal UniVersity,
Changchun 130024, China
ReceiVed December 4, 2007
In view of the above and our interest in the synthesis of carbo-
and heterocyclic compounds,10-14 the [5C + 1C],12 [5C + 1N],13
and [5C + 1S]14 annulation strategies have been developed
based on the new 1,5-bielectrophilic alkenoyl ketene-(S,S)-acetal
precursors. Recently, by combining the advantages of function-
alized ketene-(S,S)-acetals11-15 and Morita-Baylis-Hillman
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A novel temperature-controlled one-pot synthesis of substi-
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bisalkylthio-1,4-pentanedienes and ammonium acetate is
developed, and possible mechanisms leading to the divergent
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10.1021/jo702586p CCC: $40.75 © 2008 American Chemical Society
Published on Web 02/22/2008
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