title: Aza-annulation of enynyl azides: a new approach to substituted pyridines.
abstract: Synthesis of substituted pyridines through a novel aza-annulation of 2-en-4-ynyl azides, derived from MBH-acetates of acetylenic aldehydes, is described. A variety of enynyl azides having aryl, heteroaryl, and alkyl groups on the alkyne functionality successfully participated in the Ag-mediated annulation reaction to provide the corresponding 3,6-disubstituted pyridines. I2-mediated cyclization was found to be controlled by the substituent on the alkyne functionality, which offered the 5-iodo-3,6-disubstituted pyridines from enynyl azides having an electron-rich substituent on the alkyne functionality.
authors: Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology , Hyderabad 500607, India.
authors: Chada Raji
authors: CR
authors: Reddy
authors: Sujatarani A
authors: SA
authors: Panda
authors: Motatipally Damoder
authors: MD
authors: Reddy
mesh_terms: D000085:Acetates / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000085:Acetates; D000447:Aldehydes; D000480:Alkynes; D001386:Azides; D011725:Pyridines