Premium
Metal‐Free Multicomponent Construction of Tetrahydroisoquinoline‐Indole Derivatives via In Situ Generated ortho ‐Quinonoid Intermediate
Author(s) -
Kaur Pavneet,
Gurjar Kamlesh K.,
Kumar Vinod,
Gohit Sonali,
Gupta Vijay,
Kumar Rakesh
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202002802
Subject(s) - indole test , tetrahydroisoquinoline , chemistry , metal , methane , combinatorial chemistry , ligand (biochemistry) , solvent , pictet–spengler reaction , stereochemistry , organic chemistry , receptor , biochemistry
A metal‐ and ligand‐free multicomponent coupling of tetrahydroisoquinoline (THIQ), ortho ‐hydroxybenzaldehydes and indoles under solvent‐free conditions is described. The developed protocol provided a waste‐free and concise access to C(1)‐functionalized THIQ‐indole derivatives under green conditions. The reactant molar ratio and neutral conditions were found crucial for controlling the selectivity of desired THIQ‐indole product over competitive by‐products i. e . oxazine and bis(indolyl)methane. The experimental and DFT study revealed the involvement of ortho ‐quinonoid species which reacts with indoles in situ to form THIQ‐indole derivatives.