769121-30-4

Upstream product

• 71026-66-9 N-(tert-butoxycarbonyl)-1,4-phenylenediamine 
• 105-53-3 diethyl malonate 
• 4248-19-5 tert-butyl carbazate 
• 103-88-8 4-bromoacetanilide 
• 108-24-7 acetic anhydride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 106-50-3 1,4-phenylenediamine 
• 232597-42-1 tert-butyl 4-acetylphenylcarbamate 
• 756483-96-2 tert-butyl 4-acetylphenylcarbamate oxime 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 75-36-5 acetyl chloride 

Downstream Products

• 122-80-5 N-acetyl-p-phenylenediamine 
• 18144-47-3 tert-butyl 4-aminobenzoate 
• 35008-62-9 4-(N-acetylamino)phenyl isothiocyanate 

Relevant academic research and scientific papers

Thiazole ring-containing amide compounds as well as preparation method and application thereof

The invention discloses thiazole ring-containing amide compounds as well as a preparation method and application thereof, and belongs to the field of chemical technologies and pesticides. According to the present invention, p-phenylenediamine is adopted as a raw material to synthesize a series of the thiazole ring-containing amide compounds, and the synthesized thiazole ring-containing amide compounds have good inhibition effects on Xanthomonas oryzae pv.Oryza (Xoo), Xanthomonas oryzae pv.Oryzcola (Xoc) and Xanthomonas axonophora pv.Citri (Xac) in agricultural diseases and insect pests, and can be used for preparing the anti-plant bacterium agent.

An Electrochemical Beckmann Rearrangement: Traditional Reaction via Modern Radical Mechanism

Abstract: Electrosynthesis as a potential means of introducing heteroatoms into the carbon framework is rarely studied. Herein, the electrochemical Beckmann rearrangement, i. e. the direct electrolysis of ketoximes to amides, is presented for the first time. Using a constant current as the driving force, the reaction can be easily carried out under neutral conditions at room temperature. Based on a series of mechanistic studies, a novel radical Beckmann rearrangement mechanism is proposed. This electrochemical Beckmann rearrangement does not follow the trans-migration rule of the classical Beckmann rearrangement.

Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

A zinc(II)-catalyzed single-step protocol for the Beckmann rearrangement using hydroxylamine-O-sulfonic acid (HOSA) as the nitrogen source in water was developed. This direct method efficiently produces secondary amides under open atmosphere in a pure form after basic aqueous workup. It isenvironmentally benign and operationally simple.

Direct synthesis of secondary amides from ketones through Beckmann rearrangement using O-(mesitylsulfonyl)hydroxylamine

The Beckmann rearrangement is a versatile method for the preparation of secondary amides from ketones via oxime intermediates and has been widely used in the synthesis of bioactive natural products and pharmaceuticals. Herein, we have developed a highly efficient direct method for the preparation of secondary amides and lactams from ketones using O-(mesitylsulfonyl)hydroxylamine (MSH). The reactions proceed rapidly at room temperature under mild condition without requiring any additive, and tolerate multiple functional groups. A simple aqueous work-up often furnished the products in excellent yield with high purity.

o-Phthalic Anhydride/Zn(OTf)2 co-catalyzed Beckmann rearrangement under mild conditions

o-Phthalic anhydride/Zn(OTf)2 co-catalyzed Beckmann rearrangement was developed, producing the corresponding amide in up to 99% yield with acid-sensitive functionalities tolerated well, and the scale of the reaction could be enlarged to 77 mmol and the excellent yield was maintained. A successive procedure was developed. Moreover, the reaction was carried out at rt under nearly neutral conditions, and the workup was concise. These features illustrated the potential of the protocol in amide synthesis.

Scope and mechanism of a true organocatalytic beckmann rearrangement with a boronic acid/perfluoropinacol system under ambient conditions

Catalytic activation of hydroxyl functionalities is of great interest for the production of pharmaceuticals and commodity chemicals. Here, 2-alkoxycarbonyl- and 2-phenoxycarbonyl-phenylboronic acid were identified as efficient catalysts for the direct and chemoselective activation of oxime N-OH bonds in the Beckmann rearrangement. This classical organic reaction provides a unique approach to prepare functionalized amide products that may be difficult to access using traditional amide coupling between carboxylic acids and amines. Using only 5 mol % of boronic acid catalyst and perfluoropinacol as an additive in a polar solvent mixture, the operationally simple protocol features mild conditions, a broad substrate scope, and a high functional group tolerance. A wide variety of diaryl, aryl-alkyl, heteroaryl-alkyl, and dialkyl oximes react under ambient conditions to afford high yields of amide products. Free alcohols, amides, carboxyesters, and many other functionalities are compatible with the reaction conditions. Investigations of the catalytic cycle revealed a novel boron-induced oxime transesterification providing an acyl oxime intermediate involved in a fully catalytic nonself-propagating Beckmann rearrangement mechanism. The acyl oxime intermediate was prepared independently and was subjected to the reaction conditions. It was found to be self-sufficient; it reacts rapidly, unimolecularly without the need for free oxime. A series of control experiments and 18O labeling studies support a true catalytic pathway involving an ionic transition structure with an active and essential role for the boronyl moiety in both steps of transesterification and rearrangement. According to 11B NMR spectroscopic studies, the additive perfluoropinacol provides a transient, electrophilic boronic ester that is thought to serve as an internal Lewis acid to activate the ortho-carboxyester and accelerate the initial, rate-limiting step of transesterification between the precatalyst and the oxime substrate.

BENZOTHIADIAZINE COMPOUNDS

The invention is directed to substituted benzothiadiazine derivatives. Specifically, the invention is directed to compounds according to Formula (I):wherein R, R1, R2, R3, R4 and R5 are as defined herein. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, autoimmune diseases, infections, atherosclerosis, and ischemia-reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Water at elevated temperatures (WET): Reactant, catalyst, and solvent in the selective hydrolysis of protecting groups

Water at elevated temperatures (WET) can act simultaneously as reactant, solvent, and catalyst in reaction processes. WET has been successfully employed in the removal of protecting groups alleviating the need for added strong acids/bases, subsequent neutralization and waste salt elimination. The protocols for the water-mediated removal of several common protecting groups such as tert-butyl carbamates (N-Boc) from 125 to 150 °C, acetamide (N-Ac) at 275 °C and acetate esters (O-Ac) at 250 °C are reported for different model aryl compounds. In addition, high yields and selective deprotection of one protecting group in the presence of another by simply tuning the temperature is demonstrated. In order to gain further insights into reaction processes, the aqueous solubilities of several of the reactants, the kinetics and mechanisms associated with some of these reactions are also discussed. the Partner Organisations 2014.

Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis

A single set of conditions consisting of a palladium catalyst, a commercially available ligand, and a base, allow for several types of C-N bond constructions to be conducted in water with the aid of a commercially available "designer" surfactant (TPGS-750-M). Products containing a protected NH2 group in the form of a carbamate, sulfonamide, or urea can be fashioned starting with aryl or heteroaryl bromides, iodides, and in some cases, chlorides, as substrates. Reaction temperatures are in the range of room temperature to, at most, 50 °C, and result in essentially full conversion and good isolated yields.