257946-76-2

Upstream product

• 106-39-8 bromochlorobenzene 
• 765-30-0 Cyclopropylamine 
• 257946-77-3 N-cyclopropyl-N-ethyl-p-chloroaniline 
• 257946-80-8 N-cyclopropyl-N-isopropyl-p-chloroaniline 
• 208176-50-5 N-(4-chlorophenyl)-N-cyclopropylmethylamine 
• 106-47-8 4-chloro-aniline 
• 25371-91-9 2-(4-chlorophenoxy)-N-cyclopropylacetamide 
• 100-00-5 4-chlorobenzonitrile 
• 411235-57-9 cyclopropylboronic acid 
• 859504-79-3 N-cyclopropyl-N-(1,1-dideuterio)ethyl-p-chloroaniline 
• 402718-97-2 4-chloro-N-cyclopropyl-N-[1-D]isopropylaniline 
• 257946-72-8 N-(1-ethoxycyclopropyl)-4-chloroaniline 

Downstream Products

• 257946-80-8 N-cyclopropyl-N-isopropyl-p-chloroaniline 

Relevant academic research and scientific papers

Red-Light-Induced N, N'-Dipropyl-1,13-dimethoxyquinacridinium-Catalyzed [3+2] Cycloaddition of Cyclopropylamines with Alkenes or Alkynes

A red-light-mediated [3+2] annulation of cyclopropylamines with akenes or alkynes in the presence of N,N'-dipropyl-1,13-dimethoxyquinacridinium is reported. An array of cyclopentane or cyclopentene derivatives with diverse functional groups have been obta

Reductive C?N Coupling of Nitroarenes: Heterogenization of MoO3 Catalyst by Confinement in Silica

The construction of C?N bonds with nitroaromatics and boronic acids using highly efficient and recyclable catalysts remains a challenge. In this study, nanoporous MoO3 confined in silica serves as an efficient heterogeneous catalyst for C?N cross-coupling of nitroaromatics with aryl or alkyl boronic acids to deliver N-arylamines and with desirable multiple reusability. Experimental results suggest that silica not only heterogenizes the Mo species in the confined mesoporous microenvironment but also significantly reduces the reaction induction period and regulates the chemical efficiency of the targeted product. The well-shaped MoO3@m?SiO2 catalyst exhibits improved catalytic performance both in yield and turnover number, in contrast with homogeneous Mo catalysts, commercial Pd/C, or MoO3 nanoparticles. This approach offers a new avenue for the heterogeneous catalytic synthesis of valuable bioactive molecules.

Dirhodium(II)-Catalyzed (3 + 2) Cycloaddition of the N-Arylaminocyclopropane with Alkene Derivatives

Several (3 + 2) cycloaddition reactions catalyzed by dirhodium(II) complexes between N-arylaminocyclopropane and alkenes derivative have been developed. Preliminary mechanism studies suggest that dirhodium(II) complexes may decrease the bond-dissociation

COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES

The present invention provides compounds of formula I: [INSERT FORMULA HERE] or a pharmaceutically acceptable salt, tautomer, or stereoisomer, thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds and methods of using such compounds for treating, preventing, inhibiting, ameliorating, or eradicating the pathology and/or symptomology of a disease caused by a Plasmodium parasite, such as malaria.

An efficient synthesis of N-cyclopropylanilines by a smiles rearrangement

Treatment of 2-chloro-N-cyclopropylacetamide with phenols gave the corresponding 2-aryloxy-N-cyclopropylacetamides, which on treatment with a base gave the corresponding N-cyclopropylanilines. Georg Thieme Verlag Stuttgart New York.

Intermolecular [3+2] cycloaddition of cyclopropylamines with olefins by visible-light photocatalysis

It's the power of light! A visible-light-mediated intermolecular [3+2] cycloaddition of mono- and bicyclic cyclopropylamines with olefins catalyzed by [Ru(bpz)3](PF6)2·H2O has been developed to furnish aminocyclopentane derivatives in good yields (see scheme, bpz=2,2′-bipyrazine). Saturated 5,5- and 6,5-fused heterocycles are obtained in synthetically useful yields and diastereoselectivity.

Evidence for a hydrogen abstraction mechanism in P450-catalyzed N-dealkylations

The experimental evidence presented in this manuscript suggest against the widely accepted single electron/proton transfer mechanism for P450 catalyzed N-dealkylations and provides strong support for a hydrogen atom abstraction mechanism.

P450/NADPH/O2- and P450/PhlO-catalyzed N-dealkylations are mechanistically distinct

A high-valent iron-oxo species analogous to the compound I of peroxidases has been thought to be the activated oxygen species in P450-catalyzed reactions. Spectroscopic characterization of the catalytically competent iron-oxo species in iodosobenzene (PhIO)-supported model reactions and parallels between these model reactions and PhIO- and NADPH/O2-supported P450 reactions have been taken as strong evidence for this proposal. To support this proposal, subtle differences observed in regio- and chemoselectivities, isotope effects, and source of oxygen, etc., between NADPH/O2- and PhIO-supported P450 reactions have been generally attributed to reasons other than the mechanistic differences between the two systems. In the present study, we have used a series of sensitive mechanistic probes, 4-chloro-N-cyclopropyl-N-alkylanilines, to compare and contrast the chemistries of the NADPH/O2- and PhIO-supported purified CYP2B1 N-dealkylation reactions. Herein we present the first experimental evidence to demonstrate that the NADPH/O2- and PhIO-supported P450 N-dealkylations are mechanistically distinct and, thus, the P450/PhIO system may not be a good mechanistic model for P450/NADPH/O2-catalyzed N-dealkylations. Copyright

A mechanistic comparison between cytochrome P450- and chloroperoxidase-catalyzed N-dealkylation of N,N-dialkyl anilines

Most peroxidases use histidine as an axial ligand for heme, while chloroperoxidase (CPO) uses a thiolate, which is similar to the ligand employed by cytochrome P450 (P450). Several studies have also shown that, unlike other peroxidases, CPO is capable of carrying out monooxygenation reactions in a similar manner to P450 in addition to typical peroxidase-like reactions. These observations have been attributed to the similarities of the active-site architecture of the two enzymes. Both enzymes have been shown to efficiently catalyze the oxidative N-dealkylation of amines. The similar magnitudes of the kinetic isotope effects determined for P 450- and CPO-catalyzed N-dealkylation of N,N-dimethylaniline have been used to propose that these reactions proceed through similar mechanisms. In this study, we have examined the mechanism of CPO-catalyzed N-dealkylation using a series of radical probes, 4-chloro-N-cyclopropyl-N-alkylanilines 1-3, which we have recently used in the mechanistic studies of P450, and compared the results with those of P450-catalyzed reactions. The results show that P450- and CPO-catalyzed reactions proceed through distinctly different mechanisms. As previously reported, while P 450-catalyzed reactions appear to proceed through a C α-hydrogen abstraction mechanism, CPO-catalyzed reactions proceed through a single electron/proton transfer (SET/H+) mechanism, similar to reactions catalyzed by Horseradish peroxidase (HRP). Thus, CPO may not be a good mechanistic model for P450-catalyzed N-dealkylations. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

The synthesis of N-arylcyclopropylamines via palladium-catalyzed C-N bond formation

A variety of N-arylcyclopropylamines has been prepared in one step, by the Pd2(dba)3/BINAP/NaOtBu-catalyzed amination of an aryl bromide with cyclopropylamine. Compounds bearing the N-aryl substitutent (phenyl, 4-methylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-chlorophenyl, 1-napthyl, 9-anthryl, 9-phenanthryl, and 3-pyridyl) were prepared in isolated yields ranging from 43 to 99%. Overall, this chemistry represents a vast improvement over the previous multi-step procedures for the synthesis of compounds of this type.