Palladium-Catalyzed Domino Intramolecular N-Arylation/Intermolecular C-C Bond Formation for the Synthesis of Functionalized Benzodiazepinediones
A divergent and regiocontrolled Pd-catalyzed domino sequence involving an intramol. N-arylation and an intermol. Heck reaction has been developed, providing rapid access to functionalized benzodiazepine-2,5-diones, e.g. I. The starting materials were synthesized by the Ugi four-component reaction. An unprecedented X-ray structure of a bispalladacycle was documented. [on SciFinder (R)]
Cite this item
Salcedo, A., Neuville, L., Rondot, C., Retailleau, P., & Zhu, J. (2008). Palladium-Catalyzed Domino Intramolecular N-Arylation/Intermolecular C-C Bond Formation for the Synthesis of Functionalized Benzodiazepinediones. Organic Letters, 10(5), 857–860. https://doi.org/10.1021/ol7029799
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2008
10
5
857
860
CAN 148:331648
28-21
Heterocyclic Compounds (More Than One Hetero Atom)
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
1010440-27-3P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (crystal structure; prepn. of functionalized benzodiazepine-2,5-diones by regiocontrolled Pd-catalyzed domino sequence involving an intramol. N-arylation and an intermol. Heck reaction); 3375-31-3 Role: CAT (Catalyst use), USES (Uses) (prepn. of functionalized benzodiazepine-2,5-diones by Pd-catalyzed domino sequence involving Ugi four-component reaction, intramol. N-arylation, and an intermol. Heck reaction); 50-00-0 (Formaldehyde); 74-89-5 (Methylamine); 75-07-0 (Acetaldehyde); 78-84-2 (Isobutanal); 88-67-5 (2-Iodobenzoic acid); 96-33-3 (Methyl acrylate); 100-46-9 (Benzylamine); 107-13-1 (Acrylonitrile); 109-73-9 (Butylamine); 111-71-7 (Heptanal); 122-78-1 (Phenylacetaldehyde); 2680-03-7 (N,N-Dimethylacrylamide); 807355-02-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of functionalized benzodiazepine-2,5-diones by Pd-catalyzed domino sequence involving Ugi four-component reaction, intramol. N-arylation, and an intermol. Heck reaction); 1010440-18-2P; 1010440-19-3P; 1010440-20-6P; 1010440-21-7P; 1010440-22-8P; 1010440-23-9P; 1010440-24-0P; 1010440-25-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of functionalized benzodiazepine-2,5-diones by Pd-catalyzed domino sequence involving Ugi four-component reaction, intramol. N-arylation, and an intermol. Heck reaction); 1010440-26-2P Role: BYP (Byproduct), PREP (Preparation) (prepn. of functionalized benzodiazepine-2,5-diones by regiocontrolled Pd-catalyzed domino sequence involving an intramol. N-arylation and an intermol. Heck reaction); 1708-29-8 (2,5-Dihydrofuran); 7486-35-3 (Tributylvinylstannane); 13943-58-3 (Potassium ferrocyanide); 14221-01-3 (Pd(PPh3)4); 638195-28-5 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of functionalized benzodiazepine-2,5-diones by regiocontrolled Pd-catalyzed domino sequence involving an intramol. N-arylation and an intermol. Heck reaction); 638195-33-2P; 1010440-15-9P; 1010440-16-0P; 1010440-17-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of functionalized benzodiazepine-2,5-diones by regiocontrolled Pd-catalyzed domino sequence involving an intramol. N-arylation and an intermol. Heck reaction)
REVIEWED
OTHER