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The Reaction of Donor‐Acceptor Cyclopropanes with 4,7‐Dihydroindole: A New Protocol for the Synthesis of Divergent C2‐Alkylated Indoles
Author(s) -
Kilic Haydar,
Dalkilic Oguzhan
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900268
Subject(s) - trifluoromethanesulfonate , nucleophile , chemistry , acceptor , catalysis , alkylation , michael reaction , medicinal chemistry , ring (chemistry) , organic chemistry , polymer chemistry , physics , condensed matter physics
Nucleophilic ring opening reactions of donor‐acceptor cyclopropanes with 4,7‐dihydroindole ( 1 a ) were described. A series of dimethyl 2‐(2‐(1 H ‐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 1 H NMR, 13 C NMR and High Resolution Mass Spectroscopy (HRMS) techniques.