β,β-Disubstituted <i>C</i>- and <i>N</i>-Vinylindoles from One-Step Condensations of Aldehydes and Indole Derivatives
Gil Fridkin
Nicolas Boutard
William D. Lubell
10.1021/jo900526p.s001
https://acs.figshare.com/articles/journal_contribution/_Disubstituted_i_C_i_and_i_N_i_Vinylindoles_from_One_Step_Condensations_of_Aldehydes_and_Indole_Derivatives/2837047
Direct preparation of β,β-disubstituted <i>C</i>- and <i>N</i>-vinylindoles from condensation of aldehydes on indole derivatives is presented. Heating 1-methyl- and 1-benzylindole <b>3a</b>,<b>b</b> with alkyl and aryl α-branched aldehydes and TFA in acetonitrile using microwave irradiation furnished 3-vinylindoles <b>1a</b>−<b>e</b> in 18−76% yields. Under similar conditions, 3-substituted indoles <b>4a</b>−<b>c</b> provided <i>N</i>-vinylindoles <b>2a</b>−<b>h</b> in 16−98% yields.
2009-08-07 00:00:00
indoles 4
methyl
yield
Aldehyde
aldehyde
Indole DerivativesDirect preparation
benzylindole
vinylindole
acetonitrile
Condensation
Heating
Disubstituted
indole derivatives
microwave irradiation
condensation
alkyl
TFA
disubstituted
aryl