Open AccessSynthesis of Cyclohepta[b]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4H-Furo[3,2-b]indoles with Oxyallyl Cations
Author(s) -
Valentina Pirovano,
Elisa Brambilla,
Andrea Moretti,
Silvia Rizzato,
Giorgio Abbiati,
Donatella Nava,
Elisabetta Rossi
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.9b03117
Subject(s) - cycloaddition , indole test , chemistry , reagent , solvent , medicinal chemistry , catalysis , base (topology) , combinatorial chemistry , organic chemistry , mathematics , mathematical analysis
The synthesis of cyclohepta[ b ]indole derivatives through the dearomative (4 + 3) cycloaddition reaction of 2-vinylindoles or 4 H -furo[3,2- b ]indoles with in situ generated oxyallyl cations is reported. Oxyallyl cations are generated from α-bromoketones in the presence of a base and a perfluorinated solvent. Cyclohepta[ b ]indole scaffolds are obtained under mild reaction conditions, in the absence of expensive catalysts, starting from simple reagents, in good to excellent yields and with complete diasteroselectivity. Preliminary expansion of the scope to 3-vinylindoles and to aza-oxyallyl cations is reported.