60165-04-0

Usage

InChI:InChI=1/C15H14N2O2/c1-11-8-14(17(18)19)9-12(2)15(11)16-10-13-6-4-3-5-7-13/h3-10H,1-2H3/b16-10+

Upstream product

• 6425-11-2 4,4'-((4-nitrophenyl)methylene)dimorpholine 
• 87-62-7 2,6-dimethylaniline 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 135569-46-9 trans-1-(2,6-dimethylphenyl)-3-(methylphenylamino)-4-(p-nitrophenyl)-2-azetidinone 

Relevant academic research and scientific papers

Synthesis and molecular docking studies of imines as α-glucosidase and α-amylase inhibitors

Imine functionality is found in many compounds with important biological activity. Thus, the development of novel synthetic approaches for imines is important. In this work, it is propose an easy, eco-friendly and straightforward synthesis pathway of aryl imines under microwave irradiation catalyzed by Alumina-sulfuric acid. In addition, the in vitro enzymatic inhibition, antioxidant activity and molecular docking studies were performed. The aryl imines were isolated with yields in the range of 37–94%. All aryl imines synthesized were evaluated for in vitro inhibitory potential against α-glucosidase and α-amylase enzymes and the results exhibited that the most of the compounds displayed inhibitory activity against both enzymes. The (E)-1-(4-nitrophenyl)-N-(pyridin-2-yl)methanimine (3d) was 1.15-fold more active than acarbose against α-amylase whilst the (E)-1-phenyl-N-(pyridin-2-yl)methanimine (3c) displayed similar activity that acarbose against α-glucosidase. The molecular docking studies in α-glucosidase and α-amylase reveal that aryl imines mainly establish an H-bond with the R2-subtituent and hydrophobic interactions with the R1-subtituent. The docking analysis reveals these synthetic aryl imines 3d-i interact in same active site than acarbose drug in both enzymes.

Cycloaddition of (N-Alkyl-N-phenylamino)ketene with Imines

(N-Alkyl-N-phenylamino)ketenes were prepared in the presence of various imines, and a cycloaddition reaction occurred to yield 3-(N-alkyl-N-phenylamino)-2-azetidinones.The size and electronic nature of the imine substituents were varied in order to probe those factors that influence the stereochemistry of the cycloaddition.The stereochemistry of the 2-azetidinone was determined by the substitution pattern of the imines.In general, the stereochemistry of the 2-azetidinone products are significantly influenced by the bulk of the N substituent on the imine.These results are discussed in terms of a two-step zwitterionic intermediate.

THERMODYNAMIC DISSECTION OF SOLVENT EFFECTS IN THE SCHIFF REACTION

Rate constants for the reactions of p-substituted benzaldehydes with aniline and some 2-alkyl- and 2,6-dialkylanilines to give imines have been measured in acetonitrile and N,N-dimethylformamide at 25 and 75 deg C.The contributions of solvation energies to the free energy of activation have been measured at 25 deg C in cyclohexane, carbon tetrachloride, methanol, N,N-dimethylformamide, acetonitrile, ethylene glycol, dimethyl sulphoxide and N-methylformamide for the reaction of benzaldehyde and aniline.The observed reactivity depends on both polar and steric effects of the alkyl groups.Thermodynamic dissection of solvent effects points out that acidic or basic properties of solvents are important features in determining the rate of the process.However, the changeover of the rate-limiting step from the formation of the intermediate α-amino alcohol (with electron-donating groups) to its dehydration (with electron-withdrawing substituents) seems scarcely affected by solvent variations. 1H NMR measurements in dimethyl sulphoxide allowed the detection of the intermediate α-amino alcohol.

Etudes sur les composes gem-diamines-V-Reactions d'anilines sur des composes gem-dimorpholines.

A systematic study of gem-dimorpholino compounds, which produce aldehydes by hydrolysis, has shown that such compounds do indeed have aldehydic character and can be used in synthesis in place of the corresponding aldehydes.As part of this study we have examined the behaviour of such gem-dimorpholino compounds towards some nucleophilic reagents such as mercaptans, amides and anilines under acid conditions.We have found experimental conditions under which symmetrical geminal compounds are produced: dithioacetals, gem-bis(acylamino), gem-diamino and gem-diaryl compounds.We have thus developed several new synthetic methods which compare favourably with existing methods.In most cases we have been able to show that the reaction proceeds by an intermediate in which only one of the morpholino groups has been replaced by the nucleophile.In this paper we report on the condensation of some anilines with gem-dimorpholino compounds.N,N-dimethylaniline condenses with gem-dimorpholino compounds as with the corresponding aldehydes to give gem-diaryl compounds.The case of primary arylamines is remarkable for the different results obtained.As could be expected from our most recent results, most of the condensation products are complex mixtures which are either non-distillable and non-crystallisable oils or glassy solids with indistinct melting points.It is often impossible to isolate any pure chemical substance from these mixtures.We shall thus only describe certain cases: the behaviour of 2,6-xylidine is particularly interesting.Under certain conditions this aniline derivative can condense on the aromatic ring similarly to N,N-dimethylaniline.The initial product of the reaction is an aldimine or "anil".Benzaldimines which are stabilised by conjugation do not react further while phenylglyoxaldimines are transformed into gem-diaryl compounds by heating in acetic acid. 2,5-dimethoxyaniline also condenses by way of the aromatic ring to give a gem-diaryl compound but the corresponding aldimine could not be shown to be an intermediate. 2-nitro and 3-nitroaniline, in which the aromatic ring is deactivated, can only condense by the nitrogen atom to give gem-diamino compounds.In summary, we think that primary arylamines in acetic acid condense with gem-dimorpholino compounds preferentially on the nitrogen atom of the amino group.These compounds can subsequently, according to their stability, rearrange provided that the aromatic ring is activated by electron-donating substituents.It still remains to be determined if there is a definite point at which a primary aniline starts to act as an ambifunctional nucleophile.