Synthesis of furoquinolines by a multicomponent domino process

Five bonds form in one pot, from three well-designed yet readily accessible substrates. Simply mixing an o-alkynyl aniline, e.g., 2-H2NC6H4C==CCO2Me, an aldehyde, e.g., heptanal, and ammonium chloride in toluene at room temp., followed by addn. of an isocyanoacetamide, e.g., PhCH2CH(CN)COR (R = morpholino), and heating to reflux, provides the polysubstituted furo[2,3-c]quinoline, e.g. I (same R), in good to excellent yield. [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 41, 19, 3633-3635
Year:
2002
Keywords:
Note:
CAN 138:204963
28-2
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr.
Journal
1433-7851
written in English.
12125-02-9 (Ammonium chloride) Role: CAT (Catalyst use), USES (Uses) (multicomponent synthesis of furo[2,3-c]quinolines); 78-84-2 (Isobutanal); 111-71-7 (Heptanal); 123-11-5 (4-Methoxybenzaldehyde); 459-57-4 (4-Fluorobenzaldehyde); 941-69-5 (N-Phenylmaleimide); 3132-99-8 (3-Bromobenzaldehyde); 13141-38-3; 52670-38-9; 85059-38-7; 85059-48-9; 97387-41-2; 500555-97-5 Role: RCT (Reactant), RACT (Reactant or reagent) (multicomponent synthesis of furo[2,3-c]quinolines); 500555-98-6P; 500555-99-7P; 500556-06-9P; 500556-12-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (multicomponent synthesis of furo[2,3-c]quinolines); 500556-00-3P; 500556-01-4P; 500556-02-5P; 500556-04-7P; 500556-08-1P; 500556-10-5P; 500556-14-9P; 500556-16-1P; 500556-18-3P; 500556-20-7P; 500556-22-9P Role: SPN (Synthetic preparation), PREP (Preparation) (multicomponent synthesis of furo[2,3-c]quinolines)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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