Beilstein J. Org. Chem.2019,15, 642–654, doi:10.3762/bjoc.15.60
State University, Kent, OH 44242, USA 10.3762/bjoc.15.60 Abstract A series of giant tris(heteroaryl)methanes are easily assembled by one-pot three-component synthesis by simple reflux in ethanol without catalyst or additives. Diversely substituted indoles (Ar1) react with quinoline aldehydes, quinolone
aldehydes, chromone aldehydes, and fluorene aldehydes (Ar2CHO) and coumarins (Ar3) in 1:1:1 ratio to form the corresponding tris(heteroaryl)methanes (Ar1Ar2Ar3)CH along with (Ar1Ar1Ar2)CH triads. A series of new 2:1 triads were also synthesized by coupling substituted indoles with Ar2CHO. The coupling
/HPF6 and studied by NMR and by DFT and GIAO-DFT.
Keywords: model heteroarylmethylium salts; multicomponent; one-pot catalyst-free assembly; pharmacophoric triads; three-component synthesis; tris(heteroaryl)methanes; Yonemitsu-type reaction; Introduction
During the last few decades multicomponent
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Graphical Abstract
Scheme 1:
Representative examples of tris(hetero/aryl)methanes, molecular hybrids and bis(indolyl)methanes wi...