15814-19-4

Upstream product

• 120-92-3 cyclopentanone 
• 100-46-9 benzylamine 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 

Downstream Products

• 109240-88-2 N-benzyl-N-(cyclopent-1-enyl)-2-iodobenzamide 
• 256439-56-2 N-benzyl-2,2,2-trichloro-N-cyclopent-1-enyl-acetamide 
• 289895-99-4 1-(benzylamino)cyclopentanecarbonitrile 
• 124985-39-3 1-Benzyl-1-aza-spiro[4.4]nona-3,6-dien-2-one 
• 109240-94-0 C₁₉H₁₇NO 
• 1073149-76-4 N-benzyl-N-[tris(pentafluorophenyl)silyl]-N-(cyclopent-1-enyl)amine 
• 1140972-70-8 3-(2-methoxynaphthalen-1-yl)propynoic acid benzyl(cyclopent-1-enyl)amide 
• 1429044-06-3 C₂₀H₂₀N₂O₃ 
• 1429043-90-2 1-benzyl-1’-(trifluoromethylsulfonyl)-4,5-dihydro-1H,1’Hspiro[cyclopenta[b]pyrrole-3,4’-pyridin]-2(3aH)-one 
• 1429044-05-2 methyl-1-benzyl-2-oxo-2,3a,4,5-tetrahydro-1H,1'H-spiro[cyclopenta[b]pyrrole-3,4'-pyridine]-1’carboxylate 

Relevant academic research and scientific papers

Short Total Synthesis of (±)-γ-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction

An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (±)-γ-lycorane, incorporating a new intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield.

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

METHODS OF MAKING WEE1 INHIBITOR COMPOUNDS

The invention relates to a method of producing a WEE1 inhibitor of formula (1A) useful in the treatment of pathological conditions characterized by excessive cell proliferation, such as cancer. In some embodiments, the invention relates to methods for producing intermediate compounds of formulas (3), (5) and (6) as defined in the description.

Silica Gel-mediated Synthesis of β-Enamino Esters and its Application for the Synthesis of Indeno 4-Hydroxypyridin-2(1H)-Ones

The full scope of SiO2-based condensation of aliphatic or aromatic amines and β-keto esters to give β-enamino esters was examined. Functionalized linear β-enamino esters were easily obtained from SiO2-based condensation of β-keto esters and amines only after simple filtration. It was also demonstrated that cyclic β-enamino esters with 99% purity can be prepared in a practically large scale (60 g) without using silica gel column chromatography. The utility of the present method was fortified by the preparation of pharmaceutically useful indeno-4-hydroxypyridin-2(1H)-one analogue 11.

Flow microwave technology and microreactors in synthesis

A bespoke microwave reactor with a glass containment cell has been developed for performing continuous flow reactions under microwave heating. The prototype unit has been evaluated using a series of standard organic chemical transformations enabling scale-up of these chemical processes. As part of the development, a carbon-doped PTFE reactor insert was utilized to allow the heating of poorly absorbing reaction media, increasing the range of solvents and scope of reactions that can be performed in the device.

Spirocyclic dihydropyridines by electrophile-induced dearomatizing cyclization of N-alkenyl pyridinecarboxamides

On treatment with acylating or sulfonylating agents, N-alkenyl pyridine carboxamides (N-pyridinecarbonyl enamines) undergo a dearomatizing cyclization initiated by pyridine acylation and followed by intramolecular trapping of the resulting pyridinium cation. The products are spirocyclic dihydropyridines which may be further elaborated to spirocyclic heterocycles with drug-like features.

Enantioselective construction of bridged multicyclic skeletons: Intermolecular [2+2+2] cycloaddition/intramolecular diels-alder reaction cascade

Bridging a gap: A cationic rhodium(I)/ligand complex catalyzes the title reaction of alkynes and amide-linked 1,5-dienes, leading to bridged multicyclic compounds, with high chemo-, regio-, and enantioselectivity (see scheme; Bn=benzyl).

Bond rotation dynamics of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives

(Chemical Equation Presented) Barriers to rotation of the N-alkenyl bond in a series of N-cycloalkenyl-N-benzyl α-haloacetamide derivatives have been measured by variable-temperature NMR experiments. The barriers range from 10 to 18 kcal/mol, depending on ring size and on substituents on the cycloalkene and the amide. The observed trends aid in the design of substituent combinations that provide resolvable enantiomers or diastereomers at ambient temperature. The compounds undergo 4-exo and 5-endo radical cyclizations at rates that may be faster or slower than the estimated rate of N-alkenyl bond rotation in the derived radicals, depending on the substituents.

Highly enantioselective construction of axial chirality by palladium-catalyzed cycloisomerization of N- alkenyl arylethynylamides

A cationic palladium(ll)/(S)-xyl-Segphos complex catalyzes enantioselective cycloisomerizations of N-alkenyl arylethynylamldes leading to axlally chlral 4-aryl-2-pyridones In high yields with high ee values. The present catalysis represents the first enantioselective construction of axial chlrallty by the transition-metal-catalyzed cyclolsomerlzatlon.

Convergent and rapid assembly of substituted 2-pyridones through formation of N-alkenyl alkynylamides followed by gold-catalyzed cycloisomerization

(Chemical Equation Presented) A new method for the convergent and rapid assembly of substituted 2-pyridones was developed through the formation of N-alkenyl alkynylamides (amide-linked 1,5-enynes) by N-acylation of !mines with alkynoyl chlorides and the subsequent cationic Au(l)/PPh3-catalyzed cycloisomerization.