66825-16-9

Upstream product

• 124-38-9 carbon dioxide 
• 2564-06-9 N-benzyl-2-chloroacetamide 
• 2945-03-1 N-benzyl-2-bromoacetamide 
• 121767-19-9 1-Phenyl-2-aza-3-trimethylsilyloxy-1,3-butadiene 
• 79-22-1 methyl chloroformate 
• 37517-81-0 3-chloro-3-oxopropanoic acid methyl ester 
• 100-46-9 benzylamine 
• 67-56-1 methanol 
• 67045-01-6 2-benzylaminocarbonylacetic acid 
• 100-41-4 ethylbenzene 
• 108-59-8 malonic acid dimethyl ester 
• 74-88-4 methyl iodide 

Downstream Products

• 67045-01-6 2-benzylaminocarbonylacetic acid 
• 90997-13-0 methyl 3-(benzylamino)-2-diazo-3-oxopropanoate 

Relevant academic research and scientific papers

Three-Component Coupling of Aldehydes, 2-Aminopyridines, and Diazo Esters via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrido[1,2-a]pyrimidin-4-ones

Imines formed in situ from 2-aminopyridines and aldehydes undergo Rh(III)-catalyzed imidoyl C-H activation and coupling with diazo esters to give pyrido[1,2-a]pyrimidin-4-ones. Aromatic and enolizable aliphatic aldehydes were both effective substrates, and a broad range of functional groups were incorporated at different sites on the heterocyclic products. In addition, methoxy and dimethylamino functionalities could be directly installed on the pyrimidine ring by employing trimethyl orthoformate or N,N-dimethylformamide dimethyl acetal in place of the aldehyde, respectively.

Palladium-Catalyzed [3 + 2]-C-C/N-C Bond-Forming Annulation

The synthesis of bi- and tricyclic structures incorporating pyrrolidone rings is disclosed, starting from resonance-stabilized acetamides and cyclic α,β-unsaturated-γ-oxycarbonyl derivatives. This process involves an intermolecular Tsuji-Trost allylation/intramolecular nitrogen 1,4-addition sequence. Crucial for the success of this bis-nucleophile/bis-electrophile [3 + 2] annulation is its well-defined step chronology in combination with the total chemoselectivity of the former step. When the newly formed annulation product carries a properly located o-haloaryl moiety at the nitrogen substituent, a further intramolecular keto α-arylation can join the cascade, thereby forming two new cycles and three new bonds in the same synthetic operation.

Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox

Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure-plasma stability relationships in these series and to identify which enzyme(s) and which pharmacophores are critical for plasma stability. Arylesterases and carboxylesterases were identified as the main metabolic enzymes for hydroxamic acids. Finally, we suggest structural features to be introduced or removed to improve stability. This work thus provides the first medicinal chemistry toolbox (experimental procedures and structural guidance) to assess and control the plasma stability of hydroxamic acids and realize their full potential as in vivo pharmacological probes and therapeutic agents. This study is particularly relevant to preclinical development as it allows obtaining compounds equally stable in human and rodent models.

Highly enantioselective epoxidation catalyzed by cinchona thioureas: Synthesis of functionalized terminal epoxides bearing a quaternary stereogenic center

A brilliant debut! Cinchona thioureas have been reported for the first time as catalysts in the area of asymmetric oxidations. They efficiently promote an unprecedented highly enantioselective epoxidation of deactivated 1,1-disubstituted alkenes to terminal epoxides containing a quaternary stereogenic center (see scheme). Copyright

Exploring the reactivity of alkylidene malonamides: Synthesis of polyfunctionalized isoxazolidinones, aziridines and oxazolines

The reactivity of alkylidene malonamides as Michael receptors in the conjugate addition of N,O-bis(trimethylsilyl)hydroxylamine has been explored. Due to the presence of several different functionalities that may be selectively transformed, the products of the conjugate addition represent versatile intermediates for the synthesis of isoxazolidinones, aziridines, oxazolines or highly functionalized β-amino-amide derivatives. These novel molecules possessing unusual backbones may be exploited as scaffolds in the preparation of bioactive molecules. ARKAT-USA, Inc.

Novel malonamide derivatives as potent κ opioid receptor agonists

A novel series of malonamide derivatives was synthesized. These amides were shown to be potent and selective κ opioid receptor agonists.

Amide derivatives and methods of their use

Amide derivatives of the general formulae Ia and Ib: are disclosed. Pharmaceutical compositions containing these compounds, and methods for their use, inter alia, for treating and/or preventing gastrointestinal disorders, pain, and pruritus are also disclosed.

New transformations from a 3-silyloxy 2-aza-1,3-diene: Consecutive Zr- mediated retro-Brook rearrangement and reactions with electrophiles

A one-pot procedure for the transformation of the title compound to α- functionalized (silylated) and α,β-unsaturated secondary amides was described. The following steps were involved: a Zr-mediated retro-Brook rearrangement, selective deprotonation with n-BuLi on the organometallic intermediate, and trapping with electrophiles including alkyl and acyl halides and aldehydes. The electrophilic addition step occurred at a stabilized α-silyl carbanion center without affecting the near transition metal residue. In the case of aldehydes, the Peterson alkenation reaction took place on the transition metal complex in a highly stereoselective way. (C) 2000 Elsevier Science Ltd.