IBX-mediated oxidative Ugi-type multicomponent reactions: application to the N and C1 functionalization of tetrahydroisoquinoline

An Ugi-type reaction of tetrahydroisoquinoline with an isocyanide and a carboxylic acid in the presence of iodoxybenzoic acid (IBX) afforded the 1,2-diacylated adduct in good to excellent yields. E.g., in the presence of IBX, reaction of 1,2,3,4-tetrahydroisoquinoline, PhCO2H, and BnNC gave 87% 2-benzoyl-N-benzyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide (I). [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition, 46, 30, 5775-5778
Year:
2007
Keywords:
Note:
CAN 147:406662
27-17
Heterocyclic Compounds (One Hetero Atom)
ICSN,CNRS,Gif-sur-Yvette Cedex,Fr.
Journal
1433-7851
written in English.
103-49-1 (Dibenzylamine) Role: RCT (Reactant), RACT (Reactant or reagent) (dual N and C acylation of dibenzylamine by IBX-mediated oxidative Ugi-type multicomponent reactions with isocyanides and carboxylic acids); 950829-71-7P Role: SPN (Synthetic preparation), PREP (Preparation) (dual N and C acylation of dibenzylamine by IBX-mediated oxidative Ugi-type multicomponent reactions with isocyanides and carboxylic acids); 64-19-7 (Acetic acid); 65-85-0 (Benzoic acid); 88-67-5 (2-Iodobenzoic acid); 91-21-4 (1,2,3,4-Tetrahydroisoquinoline); 621-82-9 (Cinnamic acid); 637-44-5 (3-Phenylpropiolic acid); 931-53-3 (Cyclohexylisonitrile); 1138-80-3 (N-Carbobenzyloxyglycine); 2459-05-4 ((E)-4-Ethoxy-4-oxobut-2-enoic acid); 7188-38-7 (tert-Butylisonitrile); 10340-91-7 (Benzylisonitrile); 16502-01-5 (1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole); 807355-02-8; 845791-23-3 Role: RCT (Reactant), RACT (Reactant or reagent) (dual N and C1 acylation of tetrahydroisoquinoline by IBX-mediated oxidative Ugi-type multicomponent reactions with isocyanides and carboxylic acids); 1321-07-9 (Iodoxybenzoic acid) Role: RGT (Reagent), RACT (Reactant or reagent) (dual N and C1 acylation of tetrahydroisoquinoline by IBX-mediated oxidative Ugi-type multicomponent reactions with isocyanides and carboxylic acids); 950829-53-5P; 950829-54-6P; 950829-55-7P; 950829-56-8P; 950829-57-9P; 950829-58-0P; 950829-59-1P; 950829-60-4P; 950829-61-5P; 950829-62-6P; 950829-63-7P; 950829-64-8P; 950829-65-9P; 950829-66-0P; 950829-67-1P; 950829-68-2P; 950829-69-3P; 950829-70-6P Role: SPN (Synthetic preparation), PREP (Preparation) (dual N and C1 acylation of tetrahydroisoquinoline by IBX-mediated oxidative Ugi-type multicomponent reactions with isocyanides and carboxylic acids)
Laboratories:




 Record created 2010-11-25, last modified 2018-09-13


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