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J Org Chem. 2010 Oct 1;75(19):6625-30. doi: 10.1021/jo101394c.

Use of the curtius rearrangement of acryloyl azides in the synthesis of 3,5-disubstituted pyridines: mechanistic studies.

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School of Pharmacy, China Medical University, Taichung, 40402, Taiwan, Republic of China.


A series of disubstituted pyridine derivatives was synthesized from the corresponding acryloyl azides by acetic acid-promoted cycloaddition. This represents a novel and convenient synthetic approach to the symmetric 3,5-disubstituted pyridines. The nature of the substituent on the double bond and the utilized solvent were found to be crucial to the yield of pyridines. The reactivity of the acid-promoted cycloaddition increases with the presence of aryl groups, such as phenyl and pyridinyl. We also explored the comprehensive mechanism by the acid-promoted cycloaddition of (13)C-labeled cinnamoyl azide. The symmetric 3,5-disubstituted pyridines were synthesized from acryloyl azides by acetic acid-promoted trimolecular condensation.

[Indexed for MEDLINE]

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