title: Use of the curtius rearrangement of acryloyl azides in the synthesis of 3,5-disubstituted pyridines: mechanistic studies.
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 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.
authors.affiliation: School of Pharmacy, China Medical University, Taichung, 40402, Taiwan, Republic of China. thchuang@mail.cmu.edu.tw
authors.forename: Ta-Hsien
authors.initials: TH
authors.lastname: Chuang
authors.forename: Yu-Chi
authors.initials: YC
authors.lastname: Chen
authors.forename: Someshwar
authors.initials: S
authors.lastname: Pola
mesh_terms: D019342:Acetic Acid / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001386:Azides; D011725:Pyridines; D019342:Acetic Acid