Synthesis of dihydrophenanthridines by a sequence of Ugi-4CR and palladium-catalyzed intramolecular C-H functionalization

The Ugi reaction of an o-iodobenzaldehyde, an aniline, an isocyanide, and a carboxylic acid afforded alpha -acetamido-alpha -phenylacetamide in good to excellent yields. The palladium-catalyzed intramol. C-H functionalization of these adducts under ligandless conditions provided the functionalized dihydrophenanthridines. Conclusion: Highly functionalized dihydrophenanthridines are synthesized in only two steps from readily accessible starting materials in good to excellent overall yields. [on SciFinder (R)]


Published in:
Beilstein Journal of Organic Chemistry, 4, No 10, No pp given
Year:
2008
Keywords:
Note:
CAN 150:168141
27-17
Heterocyclic Compounds (One Hetero Atom)
Institut de Chimie des Substances Naturelles, CNRS,Gif-sur-Yvette,Fr.
Journal; Online Computer File
1860-5397
written in English.
3375-31-3 (Palladium diacetate); 7647-10-1 (Palladium dichloride); 72287-26-4 (Dichloro(diphenylphosphinoferrocene)palladium) Role: CAT (Catalyst use), USES (Uses) (prepn. (acyl)dihydrobenzoquinolinecarboxamides via Ugi reaction of iodobenzaldehydes with arylamines, isocyanides and carboxylic acids followed by palladium-catalyzed cyclization); 62-53-3 (Aniline); 65-85-0 (Benzoic acid); 94-09-7 (Ethyl 4-aminobenzoate); 99-09-2 (3-Nitroaniline); 100-01-6 (4-Nitroaniline); 104-94-9 (4-Methoxyaniline); 106-47-8 (4-Chloroaniline); 107-92-6 (Butanoic acid); 134-20-3 (Methyl 2-aminobenzoate); 462-08-8 (3-Amino pyridine); 535-80-8 (3-Chlorobenzoic acid); 931-53-3 (Cyclohexylisocyanide); 4530-20-5 (N-Boc glycine); 7188-38-7 (tert-Butylisocyanide); 26260-02-6 (2-Iodobenzaldehyde); 39687-95-1 (Methyl 2-isocyanoacetate); 1106813-84-6; 1106813-86-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. (acyl)dihydrobenzoquinolinecarboxamides via Ugi reaction of iodobenzaldehydes with arylamines, isocyanides and carboxylic acids followed by palladium-catalyzed cyclization); 913066-29-2P; 1106813-89-1P; 1106813-90-4P; 1106813-91-5P; 1106813-96-0P; 1106813-97-1P; 1106813-98-2P; 1106814-00-9P; 1106814-02-1P; 1106814-05-4P; 1106814-06-5P; 1106814-08-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. (acyl)dihydrobenzoquinolinecarboxamides via Ugi reaction of iodobenzaldehydes with arylamines, isocyanides and carboxylic acids followed by palladium-catalyzed cyclization); 1106814-09-8P; 1106814-11-2P; 1106814-14-5P; 1106814-16-7P; 1106814-17-8P; 1106814-19-0P; 1106814-22-5P; 1106814-24-7P; 1106814-25-8P; 1106814-27-0P; 1106814-30-5P; 1106814-31-6P; 1106814-33-8P; 1106814-34-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. (acyl)dihydrobenzoquinolinecarboxamides via Ugi reaction of iodobenzaldehydes with arylamines, isocyanides and carboxylic acids followed by palladium-catalyzed cyclization)
Laboratories:




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


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