Facile synthesis of iodopyridines from N-propargylic beta-enaminones via iodine-mediated electrophilic cyclization

KARABIYIKOĞLU S., Kelgokmen Y., ZORA M.

TETRAHEDRON, cilt.71, sa.25, ss.4324-4333, 2015 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 71 Sayı: 25
  • Basım Tarihi: 2015
  • Doi Numarası: 10.1016/j.tet.2015.04.070
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4324-4333
  • Anahtar Kelimeler: Pyridine, Iodopyridine, N-Propargylic beta-enaminone, Iodocyclization, Electrophilic cyclization, DIELS-ALDER REACTIONS, ONE-POT SYNTHESIS, DE-NOVO SYNTHESIS, C PI-BONDS, REGIOSELECTIVE SYNTHESIS, HETEROCYCLIC AZADIENES, INTRAMOLECULAR CYCLIZATION, POLYSUBSTITUTED PYRIDINES, OXIDATIVE AROMATIZATION, HETEROATOM CYCLIZATIONS
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

A facile, efficient and general synthetic method for iodopyridines is described. When treated with molecular iodine in the presence of sodium bicarbonate, N-propargylic beta-enaminones have underwent electrophilic cyclization to afford iodo-substituted pyridines in good to high yields. Iodocyclization has been found to be general for a broad range of N-propargylic beta-enaminones and tolerated the presence of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The starting N-propargylic beta-enaminones have been prepared by conjugate addition of propargylamine to alpha,beta-allcynic ketones, followed by Sonogashira coupling with aryl iodides. (C) 2015 Elsevier Ltd. All rights reserved.