The Reaction of Donor-Acceptor Cyclopropanes with 4,7-Dihydroindole: A New Protocol for the Synthesis of Divergent C2-Alkylated Indoles

KILIÇ H., DALKILIC O.

CHEMISTRYSELECT, cilt.4, sa.13, ss.3737-3740, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 4 Sayı: 13
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1002/slct.201900268
  • Dergi Adı: CHEMISTRYSELECT
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.3737-3740
  • Anahtar Kelimeler: 4, 7-Dihydroindole, Donor-Acceptor Cyclopropane, Indole, p-Benzoquinone, Ytterbium(III) trifluoromethanesulfonate, FRIEDEL-CRAFTS ALKYLATION, DIRECT C2, ARYLATION, ACID
  • Atatürk Üniversitesi Adresli: Evet

Özet

Nucleophilic ring opening reactions of donor-acceptor cyclopropanes with 4,7-dihydroindole (1 a) were described. A series of dimethyl 2-(2-(1H-indol-2-yl)-2-arylethyl)malonates were synthesized by using Ytterbium(III) trifluoromethanesulfonate as the catalyst for the first time in good to excellent yields. This study is also the first example for the reaction of donor-acceptor cyclopropanes with 4,7-dihydroindole. The obtained products are amenable to purposive elaborations. The synthesized compounds were characterized by using H-1 NMR, C-13 NMR and High Resolution Mass Spectroscopy (HRMS) techniques.