56619-95-5

Upstream product

• 3282-30-2 pivaloyl chloride 
• 100-01-6 4-nitro-aniline 
• 75-98-9 Trimethylacetic acid 
• 1516-60-5 4-nitrophenyl azide 
• 119301-86-9 --anhydrid 
• 6625-74-7 N-pivaloylaniline 
• 62-53-3 aniline 
• 100-28-7 4-Nitrophenyl isocyanate 

Downstream Products

• 104478-93-5 2,2-dimethyl-N-(4-aminophenyl)propionamide 
• 100-01-6 4-nitro-aniline 
• 1620484-63-0 N-(2-iodo-4-nitrophenyl)pivalamide 
• 1262796-61-1 C₂₁H₂₀N₂O₃ 
• 1262796-70-2 4-tert-butylphenyl N-(4-nitrophenyl)pivalimidate 
• 87223-44-7 C₁₆H₂₂N₄O₅ 

Relevant academic research and scientific papers

Traceless selenocarboxylates for the one-pot synthesis of amides and derivatives

We have recently reported a one-pot procedure for glycosyl amides synthesis using selenocarboxylate as traceless reagent. Herein, we present a further application of selenocarboxylate-azide reaction for amide bond formation on a broader range of substrates, including heterocyclic systems and fatty acid. This method proved to be highly efficient for the synthesis of primary and secondary amides, sulfonamides, imides, phosphoramide and also carbamate.

Esterification of Tertiary Amides: Remarkable Additive Effects of Potassium Alkoxides for Generating Hetero Manganese–Potassium Dinuclear Active Species

A catalyst system of mononuclear manganese precursor 3 combined with potassium alkoxide served as a superior catalyst compared with our previously reported manganese homodinuclear catalyst 2 a for esterification of not only tertiary aryl amides, but also tertiary aliphatic amides. On the basis of stoichiometric reactions of 3 and potassium alkoxide salt, kinetic studies, and density functional theory (DFT) calculations, we clarified a plausible reaction mechanism in which in situ generated manganese–potassium heterodinuclear species cooperatively activates the carbonyl moiety of the amide and the OH moiety of the alcohols. We also revealed details of the reaction mechanism of our previous manganese homodinuclear system 2 a, and we found that the activation free energy (ΔG≠) for the manganese–potassium heterodinuclear complex catalyzed esterification of amides is lower than that for the manganese homodinuclear system, which was consistent with the experimental results. We further applied our catalyst system to deprotect the acetyl moiety of primary and secondary amines.

Oxidative C?H/C?H Cross-Coupling Reactions between N-Acylanilines and Benzamides Enabled by a Cp*-Free RhCl3/TFA Catalytic System

By making use of a dual-chelation-assisted strategy, a completely regiocontrolled oxidative C?H/C?H cross-coupling reaction between an N-acylaniline and a benzamide has been accomplished for the first time. This process constitutes a step-economic and highly efficient pathway to 2-amino-2′-carboxybiaryl scaffolds from readily available substrates. A Cp*-free RhCl3/TFA catalytic system was developed to replace the [Cp*RhCl2]2/AgSbF6 system generally used in oxidative C?H/C?H cross-coupling reactions between two (hetero)arenes (Cp=pentamethylcyclopentadienyl, TFA=trifluoroacetic acid). The RhCl3/TFA system avoids the use of the expensive Cp* ligand and AgSbF6. As an illustrative example, the procedure developed herein greatly streamlines the total synthesis of the naturally occurring benzo[c]phenanthridine alkaloid oxynitidine, which was accomplished in excellent overall yield.

Rhodium(III)-catalysed, redox-neutral C(sp2)-H alkenylation using pivalimide as a directing group with internal alkynes

In the presence of [RhCp?Cl2]2, N-pivaloyl anilines react with internal alkynes to give the corresponding 2-alkenylpivalimides under redox neutral conditions through C-H activation. This redox neutral hydroarylation, which does not require an external organic acid, unlocks a regioselective synthetic route to 2-alkenyl anilines and is generally applicable to diversely substituted electron rich and electron poor pivalimides.

Regio- and Chemoselective Mono- and Bisnitration of 8-Amino quinoline Amides with Fe(NO3)3·9H2O as Promoter and Nitro Source

An efficient and regioselective remote C(5)-H nitration of 8-aminoquinoline amides by using the economical and nontoxic Fe(NO3)3·9H2O as promoter and nitro source has been developed. Furthermore, when CuCl2·2H2O was used as a catalyst, 8-aminoquinoline amides dominantly underwent bisnitration to give 5,7-dinitro-8-aminoquinoline amides. Notably, this is the first example in which Fe(NO3)3·9H2O plays a dual role as both chelating promoter and nitration reagent, and CuCl2·2H2O acts as an efficient catalyst for the bisnitration of quinolines.

Effective nitration of anilides and acrylamides by tert-butyl nitrite

Nitro compounds are important intermediates in synthetic organic chemistry and the chemical industry. Herein, the efficient copper-catalyzed [10% Cu(NO3)2·3H2O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array of functional groups were well-tolerated by this procedure. This synthetic method has many advantages, which include inexpensive starting materials, mild reaction conditions, a fast reaction rate, and high yields. A mechanistic investigation indicates that a nitro radical, which is generated from the thermal homolysis of TBN, is involved in the two nitration processes. The efficient nitration of both anilides and acrylamides was achieved by using TBN (tert-butyl nitrite) as a metal-free nitrating reagent. This synthetic method has many advantages such as mild reaction conditions, a fast reaction rate, good to excellent yields, and a broad substrate scope. Our investigation indicates that a nitro radical is involved in the reaction mechanism.

Palladium-catalyzed β-acyloxylation of simple amide via sp3 C-H activation

β-Acyloxy amides are prepared in moderate to high yields by palladium-catalyzed acyloxylation of primary sp3 C-H bonds from simple amides without any special directing group. A catalytic system of Pd(OAc)2/CF3CO2H/ K2S2O8 is available to various amides with N-substituted by linear alkanes, cyclic alkanes, and electron-deficient benzyl compounds in this reaction. Acyloxylated products could be transformed easily to the corresponding β-hydroxy amides.

Facile amide bond formation from carboxylic acids and isocyanates

Chemical equations presented. A wide variety of carboxylic acids in the form of their salts condense with aryl isocyanates at room temperature with loss of carbon dioxide to give the corresponding amides in high yield. Application of the reaction to acyl isocyanates gives unsymmetric imides. The reaction is compatible with hydroxyl groups and both Fmoc and Boc protecting groups for amines and is applicable to aliphatic, aromatic, and heteroaromatic acids.

A new class of low-molecular-weight amphiphilic gelators

A new powerful class of low-molecular-weight amphiphilic compounds has been synthesized and their structure-property relationships with respect to their gelation ability of organic solvents have been investigated. These compounds are able to gel organic solvents over a broad range of polarity. Especially polar solvents such as valeronitrile and γ-butyrolactone can be gelled even at concentrations far below 1 wt %. It was found that the gelation ability of these asymmetrically substituted p-phenylendiamines depends on a well-balanced relation of the terminal head group, the units involved in hydrogen bonding (amide or urea groups), and on the length of the alkyl chain. With this class of new gelators it is possible to tailor thermal and mechanical properties in different organic solvents and open various application possibilities.

Naphthyl-substituted and anilide-substituted sulfonamides

The present invention relates to new naphthyl- and anilide-substituted sulphonamides of the general formula (I) in which the substituents A, D, E, G, R1, R2, R3, R4and X have the meanings indicated, and to processes for their preparation and their use as antiviral agents, in particular against cytomegaloviruses.