One-pot synthesis of iodine-substituted 1,4-oxazepines

ZORA M., DİKMEN E., KELGÖKMEN Y.

TETRAHEDRON LETTERS, cilt.59, sa.9, ss.823-827, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 59 Sayı: 9
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1016/j.tetlet.2018.01.048
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.823-827
  • Anahtar Kelimeler: 1,4-Oxazepines, N-Propargylic beta-enaminones, Zinc chloride, Molecular iodine, Electrophilic cyclization, Suzuki-Miyaura reaction, PROPARGYLIC BETA-ENAMINONES, INTRAMOLECULAR CYCLIZATION, PGE(2) ANTAGONIST, POLYSUBSTITUTED PYRROLES, FACILE SYNTHESIS, ANTI-DEPRESSANT, DERIVATIVES, CHEMISTRY, AMOXAPINE, FLUORINE
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

A facile one-pot method for the synthesis of iodine-substituted 1,4-oxazepines is reported. When reacted with ZnCl2 and I-2 in DCM at 40 degrees C, N-propargylic beta-enaminones, prepared by the conjugate addition of propargylamine to alpha,beta-alkynic ketones, underwent 7-exo-dig cyclization by zinc chloride and concomitant reaction with molecular iodine to afford 2-(iodomethylene)-2,3-dihydro-1,4-oxazepines in good to high yields. This cyclization was found to occur with broad scope of substrates and high tolerance of functional groups. The resulting iodine-containing 1,4-oxazepines can be further elaborated to more complex structures by subsequent cross-coupling reactions, which may provide a platform for biological studies. (C) 2018 Elsevier Ltd. All rights reserved.