74472-27-8

Upstream product

• 111-49-9 hexamethylene imine 
• 74058-68-7 3-benzyloxycarbonyl-1,3-thiazolidine-2-thione 
• 501-53-1 benzyl chloroformate 
• 150989-58-5 2,5,6,7-Tetrahydro-1H-azepine 
• 75937-26-7 N-(benzyloxycarbonyl)-6-aminohexyl methanesulfonate 
• 2228-79-7 1,5,6,7-Tetrahydro-2H-azepin-2-one 
• 3349-62-0 cyclohex-2-enone oxime 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1227635-42-8 benzyl 2-methoxyazepane-1-carboxylate 

Relevant academic research and scientific papers

3-Acetoxyquinuclidine as Catalyst in Electron Donor-Acceptor Complex-Mediated Reactions Triggered by Visible Light

3-Acetoxyquinuclidine was found to act as a catalytic electron donor species in a variety of electron donor-acceptor complex-mediated reactions. Only substoichiometric amounts (10-25 mol %) were needed to trigger the desired reaction. The outcome could be tuned by selecting the nature of the formed radical to perform amino- and hydro-decarboxylation, dimerization, and cyclization reactions. Importantly, no external additives were needed in this reaction.

Carbamate Synthesis Using a Shelf-Stable and Renewable C1 Reactant

4-Propylcatechol carbonate is a shelf-stable, renewable C1 reactant. It is easily prepared from renewable 4-propylcatechol (derived from wood) and dimethyl carbonate (derived from CO2) using a reactive distillation system. In this work, the 4-propylcatechol carbonate is used for the two-step synthesis of carbamates under mild reaction conditions. In the first step, 4-propylcatechol carbonate is treated with an alcohol at 50–80 °C in the presence of a Lewis acid catalyst, such as Zn(OAc)2?2 H2O. With liquid alcohols, no solvent is used and with solid alcohols 2-methyltetrahydrofuran is used as solvent. In the second step, the alkyl 2-hydroxy-propylphenyl carbonate intermediates obtained react with amines at room temperature in 2-methyltetrahydrofuran, forming the target carbamates and the byproduct 4-propylcatechol, which can be recycled into a carbonate reactant.

Nickel-catalyzed reductive cyclization of alkyl dihalides

The reductive coupling protocol to intramolecular cyclization of dihaloalkanes is presented. It leads to five- and six-membered rings, with the former being more efficient. The incorporation of secondary alkyl halides generally promotes coupling efficiency. To the best of our knowledge, this is the first catalytic ring-closure reaction arising from dihaloalkanes under chemical reductive conditions.

Total Synthesis of Balanol and Designed Analogues

The total synthesis of balanol, a potent protein kinase C inhibitor isolated from the fungus Verticillium balanoides, is described.The hexahydroazepine fragment was prepared from D-serine through a sequence of reactions including the diastereoselective allylboration of a derived amino aldehyde and a base-induced 7-exo-tet ring closure as key steps.The benzophenone fragment was secured through the initial coupling of the two functionalised aromatic components through an ester linkage, followed by intramolecular nucleophilic attack of an aryl lithium derivative to form the desired ketone bridge.After coupling of the two balanol domains, the adoption of benzyl-derived protecting groups for the latent functionalities then allowed the liberation of balanol in a single step by catalytic hydrogenolysis.Finally, the newly developed synthetic strategy was applied to the synthesis of a variety of designed balanol analogues for biological evaluation. - Keywords: antitumor agents, balanol, enzyme inhibitor, natural product, total synthesis

Synthesis of (3R,4R)-3-Amino-4-hydroxyhexahydroazepine, the Chiral Constituent of the Antibiotic Ophiocordin

(3R,4R)-3-Amino-4-hydroxyhexahydroazepine (2), the optically active constituent of the antifungal antibiotic ophicordin (1), was prepared in a multistep synthesis starting from D-serine.The absolute configuration was unambigously assigned by a comparison of the synthesized stereoisomer 2 with its racemate and the chiral moiety of the antibiotic ophiocordin by enantioselective gas chromatography. Key Words: 3-Amino-4-hydroxyhexahydroazepine / Cordyceps ophioglossoides / Antifungals / Antibiotics / Ophiocordin

MONITORED AMINOLYSIS OF 3-ACYLTHIAZOLIDINE-2-THIONE : A NEW CONVENIENT SYNTHESIS OF AMIDE

3-Acylthiazolidine-2-thiones (1) were easily prepared and they were treated with several amines in dichloromethane to give amides 4 in very high yields within a short time.Aminoalcohols and aminophenols were selectively converted into acylaminoalcohols and acylaminophenols, respectively, by this reaction.One can monitor the reaction by disappearance of the yellow color of the starting material 1.Some amide alkaloids (15-18) have effectively been synthesized.