33904-02-8

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 64-18-6 formic acid 
• 709-09-1 3,4-dimethoxynitrobenzene 
• 13546-91-3 N-hydroxy-3,4-dimethoxybenzamide 
• 77287-34-4 formamide 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 6315-89-5 3,4-dimethoxyaniline 
• 2258-42-6 formyl acetic anhydride 
• 124-38-9 carbon dioxide 
• 922-67-8 propynoic acid methyl ester 
• 2043-61-0 cyclohexanecarbaldehyde 
• 66037-04-5 1-acetoxy-5-bromo-2-methoxybenzene 
• 2859-78-1 4-Bromoveratrole 
• 7368-78-7 4-bromoguaiacol 

Downstream Products

• 33904-01-7 4-isocyano-1,2-dimethoxybenzene 

Relevant academic research and scientific papers

Rhodium-catalyzed ortho C-H bond activation of arylamines for the synthesis of quinoline carboxylates

The rhodium catalyzed annulation of anilines with alkynic esters allowing for the high-yield synthesis of quinoline carboxylates with excellent regioselectivity is described. This unprecedented reaction employs either formic acid as the C1 source and reductant or copper(ii) as the oxidant and is proposed to proceed via rhodacycle of in situ generated amide and enamine ester followed by ortho C-H activation of arylamines with rhodium as the catalyst.

Design, synthesis and anticancer evaluation of 3-methyl-1H-indazole derivatives as novel selective bromodomain-containing protein 4 inhibitors

Bromodomain-containing Protein 4 (BRD4), an ‘epigenetic reader’, regulates chromatin structure and gene expression via recognizing and binding acetylated lysine in histones. BRD4 has become a therapeutic target for cancers because it promotes the expression of the tumor genes, such as c-Myc, NF-κB, and Bcl-2. In this study, a new series of 3-methyl-1H-indazole derivatives were designed via virtual screening and structure-based optimization. All compounds were synthesized and evaluated for their inhibitory activities to BRD4-BD1 and their antiproliferative effects in cancer cell lines. Among them, several compounds (such as 9d, 9u and 9w) exhibited strong BRD4-BD1 affinities and inhibition activities, and potently suppressed MV4;11 cancer cell line proliferation. Among them, compound 9d showed excellent selectivity for BRD4 and effectively suppressed c-Myc, the downstream protein of BRD4. This study provided new lead compounds for further biological evaluation on BRD4.

UiO-66 as an efficient catalyst for N-formylation of amines with CO2 and dimethylamine borane as a reducing agent

The most effective way to make the best use of CO2, is the reductive formylation of amines, as formamides have many applications in industry. A new protocol has been developed for reductive N-formylation of amines with CO2 as a C1 carbon source and DMAB (Dimethylamine borane) as a reducing agent in the presence of Zr-containing metal–organic framework (MOF) as an efficient, heterogeneous recyclable catalyst. We used UiO-66 and UiO-66-NH2 as catalysts for N-formylation of amines and observed that both the catalyst performs equally. Therefore, we continued our studies with UiO-66 as a catalyst. The UiO-66 MOF shows good catalytic activity and affording the desired formamides in good to excellent yield. This catalytic system is very efficient for several amines including primary and secondary aliphatic cyclic and aromatic amines. Moreover, the prepared catalyst was recycled up to four recycled without a considerable decrease in catalytic activity.

Cu@U-g-C3N4 Catalyzed Cyclization of o-Phenylenediamines for the Synthesis of Benzimidazoles by Using CO2 and Dimethylamine Borane as a Hydrogen Source

Abstract: This work reports a green and sustainable route for the synthesis of benzimidazoles via C–N bond formation using carbon dioxide (CO2) as a C1 carbon source. In this work, Cu@U-g-C3N4 catalyst was prepared from urea derived porous graphitic carbon?nitride (U-g-C3N4) and CuCl2 and characterized by FT-IR, XRD, XPS, SEM, TPD etc. The Cu@U-g-C3N4 as a heterogeneous recyclable catalyst has been employed first time for the cyclization of o-phenylenediamines (OPD) with CO2 to benzimidazoles using dimethylamine borane (DMAB). The proposed protocol becomes sustainable and efficient due to the use of propylene carbonate/water as a suitable biodegradable, economical and environmentally benign solvent system. The proposed catalytic system showed a wide range of substrate scope for the synthesis of benzimidazoles in good to excellent yields. Graphical Abstract: [Figure not available: see fulltext.]

Consecutive Lossen rearrangement/transamidation reaction of hydroxamic acids under catalyst- and additive-free conditions

The Lossen rearrangement is a classic process for transforming activated hydroxamic acids into isocyanate under basic or thermal conditions. In the current report we disclosed a consecutive Lossen rearrangement/transamidation reaction in which unactivated hydroxamic acids were converted into N-substituted formamides in a one-pot manner under catalyst- and additive-free conditions. One feature of this novel transformation is that the formamide plays triple roles in the reaction by acting as a readily available solvent, a promoter for additive-free Lossen rearrangement, and a source of the formyl group in the final products. Acyl groups other than formyl could also be introduced into the product when changing the solvent to other low molecular weight aliphatic amide derivatives. The solvent-promoted Lossen rearrangement was better understood by DFT calculations, and the intermediacy of isocyanate and amine was supported well by experiments, in which the desired products were obtained in excellent yields under similar conditions. Not only monosubstituted formamides were synthesized from hydroxamic acids, but also N,N-disubstituted formamides were obtained when secondary amines were used as precursors.

SMALL MOLECULE INHIBITORS OF SPLEEN TYROSINE KINASE (SYK)

no abstract published

Amine modified mesoporous Al2O3@MCM-41: An efficient, synergetic and recyclable catalyst for the formylation of amines using carbon dioxide and DMAB under mild reaction conditions

This work reports an amine modified meso Al2O3@MCM-41, particularly the ordered mesoporous silica, as a catalyst for the formylation of amines with carbon dioxide (CO2) and with dimethylamine-borane (DMAB) as a green reducing source. This newly developed catalytic system represents a heterogeneous and environmentally benign protocol. Besides this, the catalyst could be reused for five consecutive cycles without any significant loss in its catalytic activity towards the synthesis of formamides. The amine modified meso Al2O3@MCM-41 catalysts were well characterized by high and low angle XRD, temperature programmed desorption (TPD), BET-surface area, TGA/DTA and FT-IR analysis techniques. The effect of various reaction parameters such as temperature, CO2 pressure, time and the ratio of substrates to DMAB for the synthesis of formamides has been investigated. The developed protocol can be applicable for the synthesis of most important key intermediates like formoterol, orlistat, leucovarin and iguratimod in biologically active compounds.

A Catalyst-Free Process for the Direct Oxidative Synthesis of Form-anilides from Arylamines and Aldehydes under Air Atmosphere

An efficient and catalyst-free process for the direct oxidative synthesis of formanilides from primary aromatic amines and aliphatic aldehydes has been developed under mild aerobic oxidation conditions. The isotope-labeling experiments indicated that the oxygen atom of the formanilide originated from dioxygen.

Highly efficient rhodium-catalyzed transfer hydrogenation of nitroarenes into amines and formanilides

An efficient and selective rhodium-catalyzed transfer hydrogenation of nitroarenes with formic acid as the hydrogen source to give amines or formanilides has been developed. The addition of iodide ion accelerates the reaction, which can take place at room temperature. Georg Thieme Verlag Stuttgart New York.

Silica supported perchloric acid catalyzed rapid N-formylation under solvent-free conditions

A rapid and chemoselective method for the N-formylation of structurally diverse amines with formic acid using silica supported perchloric acid (HClO4-SiO2) at room temperature and under solvent-free conditions has been developed. The catalyst was found to be compatible with different functional groups and the formylation proceeded smoothly with amines bearing electron withdrawing as well as electron donating substituents.