Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines

Ismailoglu E., Mert Z., Dinc M., Kaya K., Yücel B.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, cilt.2021, sa.29, ss.4107-4124, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 2021 Sayı: 29
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1002/ejoc.202100483
  • Dergi Adı: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Chimica
  • Sayfa Sayıları: ss.4107-4124
  • Anahtar Kelimeler: 1,3-Dithiane, A3-coupling, Iodocyclization, Iodothiophene, Sulfonium ion
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30-87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30-94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A(3)-coupling reaction.