The Journal of organic chemistry

Use of the Curtius Rearrangement of Acryloyl Azides in the Synthesis of 3, 5-Disubstituted Pyridines: Mechanistic Studies

TH Chuang, YC Chen, S Pola

Index: Chuang, Ta-Hsien; Chen, Yu-Chi; Pola, Someshwar Journal of Organic Chemistry, 2010 , vol. 75, # 19 p. 6625 - 6630

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Citation Number: 14

Abstract

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 ...