33905-47-4

Upstream product

• 100-44-7 benzyl chloride 
• 122-98-5 2-Anilinoethanol 
• 758640-21-0 N-Benzylaniline 
• 107-21-1 ethylene glycol 
• 540-51-2 2-bromoethanol 
• 87100-28-5 pinacol benzylboronate 
• 87-72-9 D-Xylose 
• 56-81-5 glycerol 
• 1426958-04-4 4,4,5,5-tetramethyl-N-phenyl-N-(phenylmethyl)-1,3,2-dioxaborolan-2-amine 
• 62-53-3 aniline 

Downstream Products

• 128194-11-6 (S)-2-ethyl 5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-1-methoxymethyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylate 
• 961-71-7 Antergan 
• 109388-15-0 methyl cis-1,2-diphenylpyrrolidine-3-carboxylate 
• 51-50-3 N,N-dibenzyl-2-chloroethanamine 
• 109651-07-2 1-(N,N-dibenzylamino)-2-iodoethane 

Relevant academic research and scientific papers

Aza-Matteson Reactions via Controlled Mono-and Double-Methylene Insertions into Nitrogen-Boron Bonds

Boron-homologation reactions represent an efficient and programmable approach to prepare alkylboronates, which are valuable and versatile synthetic intermediates. The typical boron-homologation reaction, also known as the Matteson reaction, involves formal carbenoid insertions into C-B bonds. Here we report the development of aza-Matteson reactions via carbenoid insertions into the N-B bonds of aminoboranes. By changing the leaving groups of the carbenoids and altering Lewis acid activators, selective mono- and double-methylene insertions can be realized to access various α- and β-boron-substituted tertiary amines, respectively, from common secondary amines. The derivatization of complex amine-containing bioactive molecules, diverse functionalization of the boronate products, and sequential insertions of different carbenoids have also been achieved.

Ru-Catalyzed Switchable N-Hydroxyethylation and N-Acetonylation with Crude Glycerol

Highly efficient Ru-catalyzed selective C?C or C?O bond cleavage of polyols (e.g., crude glycerol) for N-hydroxyethylation or N-acetonylation of amines was achieved through the hydrogen-borrowing approach. A variety of amines were transformed to the desired amino alcohols/ketones in moderate-to-excellent yields, opening up new avenues for generation of oxygenated pharmaceuticals and fine chemicals from renewable raw materials. The use of new redox-active catalysts containing bisphosphine/thienylmethylamine ligands allows this hydrogen-borrowing system to be operated selectively under both basic and acidic conditions.

Direct hydroxyethylation of amines by carbohydrates: Via ruthenium catalysis

An efficient and halogen-free catalytic methodology for the synthesis of β-amino alcohols from aromatic amines and biomass-derived carbohydrates is demonstrated for the first time. The activation of C5/C6 sugars by a ruthenium catalyst selectively generates the C2 alkylating reagent glycolaldehyde. The transformation involves metal-catalyzed hydrogen borrowing for the reduction of the imine intermediate. A series of arylamines bearing various substituents were successfully transformed into the desired products in good to excellent yields.

Transition Metal-Catalysed Intramolecular Carbenoid C?H Insertion for Pyrrolidine Formation by Decomposition of α-Diazoesters

The use of Pd-, Rh(II)- and Ru(II)-based catalysts has been explored in the transition metal-catalysed intramolecular carbenoid C?H insertion of α-diazoesters leading to pyrrolidines. Although the outcome of the reaction was highly substrate-dependent, in general, it was possible to control the chemoselectivity of the process towards pyrrolidines by adequate catalyst selection. The Pd(0)-catalysts were as efficient as [Rh(Ph3CCO2)2]2 in promoting the C(sp3)?H insertion of ortho-substituted anilines. In contrast, for anilines bearing meta- and para-substituents, the Rh(II)-catalyst provided the best chemoselectivities and reaction yields. On the other hand, [Ru(p-cymene)Cl2]2 was the most efficient catalyst for the insertion reaction of the N-benzyl-N-phenyl and N,N-dibenzyl α-diazoesters, while the C(sp3)?H insertion of the N-benzylsulfonamide substrate was only promoted by [Rh(Ph3CCO2)2]2. According to density functional theory (DFT) calculations, the mechanism involved in the Pd(0)- and Ru(II)-catalysed C(sp3)?H insertions differs considerably from that typically proposed for the Rh(II)-catalysed transformation. Whereas the Pd(0)-catalysed reaction involves a Pd-mediated 1,5-H migration from the C(sp3)?H bond to the carbenoid carbon atom leading to the formal oxidation of the transition metal, a Ru(II)-promoted Mannich type reaction involving a zwitterionic intermediate seems to be operative in the Ru(II)-catalysed transformation. (Figure presented.).

Copper-catalyzed N- and O-alkylation of amines and phenols using alkylborane reagents

By the reaction of amines with alkylborane reagents in the presence of a catalytic amount of copper(II) acetate Cu(OAc)2 and di-tert-butyl peroxide, a cross-coupling reaction proceeded and alkylated amines were obtained in good to excellent yields. Phenols are also applicable for this reaction, and the corresponding alkyl aryl ethers were produced.

Ruthenium-catalyzed /V-alkylation of amines and sulfonamides using borrowing hydrogen methodology

The alkylation of amines by alcohols has been achieved using 0.5 mol percent [Ru(p-cymene)CI2]2 with the bidentate phosphines dppf or DPEphos as the catalyst. Primary amines have been converted into secondary amines, and secondary amines into tertiary amines, including the syntheses of Piribedil, Tripelennamine, and Chlorpheniramine. A/-Heterocyclization reactions of primary amines are reported, as well as alkylation reactions of primary sulfonamides. Secondary alcohols requiremore forcing conditions than primary alcohols but are still effective a lkylating agents in the presence of this catalyst.

SUBSTITUTED ARYLALKANOIC ACID DERIVATIVE AND USE THEREOF

A compound represented by the formula (I)[In the formula, Link represents a saturated or unsaturated straight hydrocarbon chain having 1 to 3 carbon atoms, C2 to C6 in the aromatic ring (E) independently represent a ring-constituting carbon atom, one of the ring-constituting carbon atoms may be replaced with V, V represents nitrogen atom, or carbon atom substituted with Zx, Zx represents a saturated alkyl group having 1 to 4 carbon atoms and the like, Rs represents -D-Rx etc., D represents a single bond, oxygen atom and the like, Rx represents a saturated alkyl group having 3 to 8 carbon atoms and the like, AR represents a partially unsaturated or completely unsaturated condensed bicyclic carbon ring or a heterocyclic ring, and Y represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms and the like] or a salt thereof. A compound having prostaglandin production-suppressing action and leukotriene production-suppressing action is provided.

Design and synthesis of imidazoline derivatives active on glucose homeostasis in a rat model of type ii diabetes. 2. Syntheses and biological activities of 1,4-dialkyl-, 1,4-dibenzyl, and 1-benzyl-4-alkyl-2-(4',5'- dihydro-1'H-imidazol-2'-yl)piperazines and isosteric analogues of imidazoline

Piperazine derivatives have been identified as new antidiabetic compounds. Structure-activity relationship studies in a series of 1-benzyl- 4-alkyl-2-(4',5'-dihydro-1'H-imidazol-2'-yl)piperazines resulted in the identification of 1-methyl-4-(2',4'-dichlorobenzyl)-2-(4',5'-dihydro-1'H- imidazol-2'-yl)piperazine, PMS 812 (S-21663), as a highly potent antidiabetic agent on a rat model of diabetes, mediated by an important increase of insulin secretion independently of α2 adrenoceptor blockage. These studies were extended to find additional compounds in these series with improved properties. In such a way, substitution of both piperazine N atoms was first optimized by using various alkyl, branched or not, and benzyl groups. Second, some modifications of the imidazoline ring and its replacement by isosteric heterocycles were carried out, proceeding from PMS 812, to evaluate their influence on the antidiabetic activity. The importance of the distance between the imidazoline ring and the piperazine skeleton was studied third. Finally, the influence of the N-benzyl moiety was also analyzed compared to a direct N-phenyl substitution. The pharmacological evaluation was performed in vivo using glucose tolerance tests on a rat model of type II diabetes. The most active compounds were 1,4-diisopropyl-2-(4',5'-dihydro-1'H-imidazol-2'- yl)piperazine (41a), PMS 847 (S-22068), and 1,4-diisobutyl-2-(4',5'-dihydro- 1'H-imidazol-2'-yl)piperazine (41b), PMS 889 (S-22575), which strongly improved glucose tolerance without any side event or hypoglycemic effect. More particularly, PMS 847 proved to be as potent after po (100 μmol/kg) as after ip administration and appears as a good candidate for clinical investigations.

Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs

Quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal anti-inflammatory drugs (NSAIDs) are disclosed. These esters and thioesters display the anti--inflammatory profile of the parent NSAIDs with greatly reduced gastrointestinal irritancy, providing a more favorable separation of therapeutic activity and toxicological side effects than the parent NSAIDs.

Rubine disazo acid dyes for polyamides

Dyes of the formula STR1 wherein B and D are each independently 1,4-phenylene or 1,4-naphthylene; M is hydrogen, lithium, sodium, potassium or ammonium; A1 is hydrogen, C1-4 alkoxy, C1-4 alkyl, trifluoromethyl, nitro, chloro, bromo, cyano, or hydroxy; B1 and B2 are each hydrogen, C1-3 alkoxy, C1-3 alkyl, chloro or bromo; D1 is hydrogen, C1-4 alkoxy, C1-4 alkyl, or chloro; D2 is hydrogen, C1-4 alkoxy, C1-4 alkyl, chloro, bromo, fluoro, or acylamino, acyl being C1-5 alkanoyl, C1-5 alkylsulfonyl, benzoyl or benzenesulfonyl, each acyl unsubstituted or substituted with 1 to 3 of C1-2 alkyl, C1-2 alkoxy, chloro, bromo, cyano, or hydroxy; and R1 and R2 are each C1-6 alkyl, C1-6 chloro or bromoalkyl, C2-6 hydroxy- or dihydroxyalkyl, C2-6 alkoxyalkyl, C1-6 cyanoalkyl, or phenyl-C1-2 alkyl (phenyl unsubstituted or substituted with 1 to 3 of C1-2 alkyl, C1-2 alkoxy, chloro, bromo, cyano or hydroxy) are useful in dyeing natural and synthetic polyamide fibers in deep and level shades of red to blue.