27845-49-4

Upstream product

• 22483-21-2 isobutylidenebenzylamine 
• 78-81-9 isobutylamine 
• 100-52-7 benzaldehyde 
• 1077-18-5 N-benzylidenebutan-1-amine 
• 20767-31-1 benzyl(triphenyl)phosphonium bromide 
• 100-46-9 benzylamine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 42882-36-0 benzyl(2-methylpropyl)amine 
• 78-81-9 isobutylamine 
• 100522-27-8 2-(benzyl-isobutyl-amino)-ethanol 
• 23530-81-6 benzyl-isobutyl-amine; hydrochloride 
• 131196-29-7 N-(1-phenyl-3-butenyl)isobutylamine 
• 625-43-4 2-methylpropyl(methyl)amine 
• 304-19-8 (N-isobutyl)phthalimide 
• 121238-79-7 N,N-dibenzyl-2-methylpropan-1-amine 
• 106712-00-9 cis-N-isobutyl-3-phenyl-4-carboxy-3,4-dihydro-1(2H)-isoquinolone 

Relevant academic research and scientific papers

Hit-to-Lead Studies for the Antimalarial Tetrahydroisoquinolone Carboxanilides

Phenotypic whole-cell screening in erythrocytic cocultures of Plasmodium falciparum identified a series of dihydroisoquinolones that possessed potent antimalarial activity against multiple resistant strains of P. falciparum in vitro and show no cytotoxicity to mammalian cells. Systematic structure-activity studies revealed relationships between potency and modifications at N-2, C-3, and C-4. Careful structure-property relationship studies, coupled with studies of metabolism, addressed the poor aqueous solubility and metabolic vulnerability, as well as potential toxicological effects, inherent in the more potent primary screening hits such as 10b. Analogues 13h and 13i, with structural modifications at each site, were shown to possess excellent antimalarial activity in vivo. The (+)-(3S,4S) enantiomer of 13i and similar analogues were identified as the more potent. On the basis of these studies, we have selected (+)-13i for further study as a preclinical candidate.

Fast transimination in organic solvents in the absence of proton and metal catalysts. A key to imine metathesis catalyzed by primary amines under mild conditions

Amine-imine exchange reactions of sterically unhindered reactants were found to be surprisingly fast at room temperature in a variety of nonaqueous solvents in the absence of proton and metal catalysts. The reaction mechanism suggested by ab initio calculations in the gas phase involves nucleophilic addition to the CN bond in concert with proton transfer from the amine NH bond to the imine nitrogen via a highly imbalanced transition state. These very fast transimination reactions were utilized in the catalysis of imine metathesis. Imine metathesis, usually carried out in organic solvents at high temperature in the presence of metal catalysts, occurs smoothly at room temperature in the presence of primary amines under nonacidic conditions as a result of coupled transimination processes. Kinetic data fully consistent with the proposed reaction mechanism were obtained.

General, green, and scalable synthesis of imines from alcohols and amines by a mild and efficient copper-catalyzed aerobic oxidative reaction in open air at room temperature

A general, green, and scalable synthesis of the useful imines and a,b-unsaturated imines is successfully achieved by a low-loading and powerful, mild and efficient copper-catalyzed aerobic oxidative reaction of alcohols and amines in the open air at room temperature under base- and dehydrating reagent-free conditions. This practical reaction can use air as the economic and green oxidant, tolerates a wide range of substrates, can afford high yields of the target imines on a large scale, and produces water as the only by-product, and thus being the best imination method as yet using alcohols and amines directly.

Direct and mild palladium-catalyzed aerobic oxidative synthesis of imines from alcohols and amines under ambient conditions

By ligand, TEMPO, and base screening, we developed a mild and green one-pot imine synthesis from alcohols and amines via a low-loading palladium-catalyzed tandem aerobic alcohol oxidation-dehydrative condensation reaction that can be readily carried out in open air at room temperature.

Base induced carbon-nitrogen (C=N) double bond migration in Schiff bases

Various Schiff bases have been prepared to study base induced carbon-nitrogen double bond migrations. Schiff bases derived from aliphatic aldehydes display highest selectivity. Hydrolysis of the resulting rearranged Schiff base provides an entry to make amines from aldehydes. The reaction has possible practical application.

In Situ Oxidation-Imine Formation-Reduction Routes from Alcohols to Amines

(matrix presented) Manganese dioxide is employed as an in situ oxidant for the one-pot conversion of alcohols into imines. In combination with polymer-supported cyanoborohydride (PSCBH), a one-pot oxidation-imine formation-reduction sequence is reported. This procedure enables alcohols to be converted directly into both secondary and tertiary amines.

1,3-Dipolar Cycloaddition of Imidate Ylides on Imino-Alcohols: Synthesis of New Imidazolones Using Solvent Free Conditions.

Imidates derived from α-amino esters as potential azomethine ylides, undergo 1,3-dipolar cycloaddition with imino-alcohols, in tautomeric equilibrium with 1,3-oxazolidines, without solvent at 70 deg C or under microwave irradiation.This reaction leads to a wide range of novel polyfunctionalized 4-yliden-2-imidazolin-5-ones in good yields with short reaction times.The reactivity of these imidates derived from α-amino esters with imino-alcohols is rationalized from the energy of the Frontier Molecular Orbitals (FMO) determined by semi-empirical PM3 calculations : the reaction is controlled by the interaction HOMO(1,3-dipole) - LUMO(dipolarophile) and the second order perturbation energy calculations are in agreement with the experimental reaction orientation.

Reaction of Thioaldehydes with Amines

The reaction of phosphonium ylides with elemental sulfur gave thioaldehydes, which changed to the corresponding thioamides in good yields when treated with amines.When thioaldehydes containing α-hydrogens were treated with secondary amines, the corresponding enamines or reduction products were obtained.

The Addition of γ-(Trimethylsilyl)allylboronates to Imines

The addition of γ-(trimethylsilyl)allylboronates to imines is described and compared with the addition of simple allylboronates to imines.The addition of γ-(trimethylsilyl)allylboronates is found to be more efficient than the addition of simple allylboronates to imines.The stereoselectivity is dependant upon the nature of the imine; imines derived from aromatic aldehydes give anti products and imines derived from aliphatic aldehydes give syn products.Proof of stereochemistry was established by conversion of the anti and syn derivatives to their respective Z- and E-dienes by a methylation/E-2 elimination process.With α-alkoxy aldehydes the reaction proceeds with excellent selectivity giving the product of Felkin-Ahn addition.