Three-component synthesis of polysubstituted 6-azaindolines and its tricyclic derivatives

By simply heating a toluene soln. of isocyanoacetamide, amine, and aldehyde, a clean three-component reaction occurred to provide the 6-azaindolines and pyrrolidinone-fused 6-azaindolines. E.g., heating a mixt. of morpholine, heptanal, and isocyanoacetamide I gave 61% 6-azaindoline II. In this multicomponent reaction, the isocyanoacetamide reacted four times in a highly ordered manner creating three heterocyclic rings with the concurrent formation of five chem. bonds and a minimal loss of mol. wt. Heating is the only external energy required to promote this powerful complexity-generating MCR. [on SciFinder (R)]


Published in:
Organic Letters, 7, 2, 239-242
Year:
2005
Keywords:
Note:
CAN 142:197927
28-2
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
written in English.
62-53-3 (Aniline); 100-46-9 (Benzylamine); 100-52-7 (Benzaldehyde); 109-73-9 (Butylamine); 110-89-4 (Piperidine); 110-91-8 (Morpholine); 111-71-7 (Heptanal); 120-20-7; 123-11-5 (4-Methoxybenzaldehyde); 555-16-8 (4-Nitrobenzaldehyde); 2043-61-0 (Cyclohexanecarbaldehyde); 3132-99-8 (3-Bromobenzaldehyde); 4289-95-6 (DL-Phenylalanine, n-formyl-); 17150-62-8; 67421-74-3; 123613-53-6; 142301-77-7 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of 6-azaindolines and pyrrolidinone-fused 6-azaindolines by three-component reaction of isocyanoacetamides, amines, and aldehydes); 836678-76-3P; 836678-77-4P; 836678-78-5P; 836678-79-6P; 836678-80-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of 6-azaindolines and pyrrolidinone-fused 6-azaindolines by three-component reaction of isocyanoacetamides, amines, and aldehydes); 836678-81-0P; 836678-82-1P; 836678-83-2P; 836678-84-3P; 836678-85-4P; 836678-86-5P; 836678-87-6P; 836678-88-7P; 836678-89-8P; 836678-90-1P; 836678-91-2P; 836678-92-3P; 836678-93-4P; 836678-94-5P; 836678-95-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of 6-azaindolines and pyrrolidinone-fused 6-azaindolines by three-component reaction of isocyanoacetamides, amines, and aldehydes)
Laboratories:




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


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