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, vol.4, no.13, pp.3737-3740, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 4 Issue: 13
  • Publication Date: 2019
  • Doi Number: 10.1002/slct.201900268
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3737-3740
  • Keywords: 4, 7-Dihydroindole, Donor-Acceptor Cyclopropane, Indole, p-Benzoquinone, Ytterbium(III) trifluoromethanesulfonate, FRIEDEL-CRAFTS ALKYLATION, DIRECT C2, ARYLATION, ACID
  • Ataturk University Affiliated: Yes

Abstract

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.