52745-10-5

Upstream product

• 552-16-9 ortho-nitrobenzoic acid 
• 100-46-9 benzylamine 
• 610-14-0 2-nitrobenzyl chloride 
• 31204-05-4 2-nitrobenzoic acid 4-nitrophenyl ester 

Downstream Products

• 150483-54-8 N-benzyl-2-nitrosobenzamide 
• 5471-20-5 2-amino-N-benzylbenzamide 
• 5388-11-4 3-benzyl-3H-quinazolin-4-one 
• 1932-42-9 3-benzylquinazoline-2,4-dione 
• 23942-38-3 4-benzyl-3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-a]quinazolin-5(1H)-one 
• 1350616-38-4 3'-benzyl-1'H,2H-spiro[acenaphthylene-1,2'-quinazoline]-2,4'(3'H)-dione 
• 1848-46-0 2-benzyl-1,2-dihydro-3H-indazol-3-one 
• 1347035-20-4 N-benzyl-2-(benzylamino)benzamide 
• 401466-91-9 6-benzyl-6,6a-dihydro-9,10-dimethoxyisoindolo[2,1-a]quinazoline-5,11-dione 
• 74882-52-3 2-benzylidene-1-(2-methoxycarbonylphenyl)hydrazine 
• 4036-59-3 2-benzylidene-1-(2-carboxyphenyl)hydrazine 
• 936025-26-2 tert-butyl (S)-1-(N-benzyl-2-nitrobenzamido)-1-oxopropan-2-ylcarbamate 

Relevant academic research and scientific papers

One-Pot Synthesis of Seven-Membered Heterocyclic Derivatives of Diazepines Involving Copper-Catalyzed Rearrangement Cascade Allyl-Amination

A novel and efficient method has been proposed for the synthesis of 1,4-benzodiazepine-5-ones from o-nitrobenzoic N-allylamides by using molybdenyl acetylacetonate and copper(II) trifluoromethanesulfonate as catalysts in the presence of triphenylphosphine. This synthesis process involves nitrene formation, C-H bond insertion, C≠C bond rearrangement, and C-N bond formation cascade reactions via copper- and molybdenum-catalyzed mediation. The method features a wide substrate scope and a moderate to high yield (up to 90%), exhibiting the possibility for practical applications.

A B2(OH)4-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library

Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B2(OH)4-mediated reductive N-N b

An Efficient Catalytic Amidation of Esters Promoted by N-Heterocyclic Carbenes

An efficient NHC-catalyzed amidation between esters and amines or hydrazines is described. This strategy was tolerant for a wide scope of substrates, affording a series of amides (or hydrazides) in good to excellent yields (60-96%) under simple conditions. The approach was also used to synthesize the pharmaceutically relevant antidepressant moclobemide in 85% yield.

Conformationally restricted quinazolone derivatives as PI3Kδ-selective inhibitors: the design, synthesis and biological evaluation

A series of structurally novel quinazolone-based PI3Kδ-selective inhibitors were designed and synthesized via the approach of conformational restriction. The majority of them exhibited two-digit to single-digit nanomolar IC50 values against PI3Kδ, along with low micromolar to submicromolar GI50 values against human malignant B-cell line SU-DHL-6. The representative compound, with the most potent PI3Kδ inhibitory activity (IC50 = 6.3 nM) and anti-proliferative activity (GI50 = 0.21 μM) in this series, was further evaluated for its PI3Kδ selectivity, capability to down-regulate PI3K signaling in SU-DHL-6 cells, in vitro metabolic stability, and pharmacokinetic (PK) properties. The experimental results illustrated that this compound, as a promising lead, merits extensive structural optimization for exploring novel PI3Kδ-selective inhibitors as clinical candidates.

Preparation method of amide compounds

The invention relates to a preparation method of amide compounds. The method comprises the followings steps: feeding n-heterocyclic carbine and alkali into a reactor filled with an organic solvent inan inert gas atmosphere, stirring, sequentially feeding organic acid ester and organic amine, performing extraction through an extraction agent after reaction is accomplished, and performing chromatographic purification on residual crude products through a silicagel column, so as to obtain the amide compounds. Compared with the prior art, the method has the advantages that the n-heterocyclic carbine is taken as a catalyst, ester and amine compound rapidly form the corresponding amide compounds in the presence of the organic solvent, the reaction condition is mild, amide preparation flow is simpler and more efficient, environmentally friendly, and non-irritant, and does not generate an anaphylactic substance, the total yield is high, and volume production is easy to realize.

Poly(methylhydrosiloxane) as a green reducing agent in organophosphorus-catalysed amide bond formation

Development of catalytic amide bond formation reactions has been the subject of the intensive investigations in the past decade. Herein we report an efficient organophosphorus-catalysed amidation reaction between unactivated carboxylic acids and amines. Poly(methylhydrosiloxane), a waste product of the silicon industry, is used as an inexpensive and green reducing agent for in situ reduction of phosphine oxide to phosphine. The reported method enables the synthesis of a wide range of secondary and tertiary amides in very good to excellent yields.

Sulfur–Fluoride Exchange (SuFEx)-Mediated Synthesis of Sterically Hindered and Electron-Deficient Secondary and Tertiary Amides via Acyl Fluoride Intermediates

Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of “SuFExAmide”: a new sulfur–fluoride exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yields from sterically hindered and electron-deficient amines. The straightforward method offers significant benefits over existing protocols in terms of substrate scope, efficiency and ease of operation and is demonstrated by the synthesis of 44 amides, including GNF6702, an antiprotozoal drug candidate. In the majority of cases, the amide products are obtained in high yield without the need for excess reagents or chromatographic purification.

A novel highly stereoselective synthesis of 2,3-disubstituted 3H-quinazoline-4-one derivatives

Figure presented An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with α-amino acids followed by reductive cyclization affords enantiomerically pure (ee >93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.

1,2-Benzisoxazol-3-yl Diphenyl Phosphate: A New, Reactive Activating Agent for the Synthesis of Amides, Esters, and Peptides via Condensation

A new activating agent for condensations, 1,2-benzisoxazol-3-yl diphenyl phosphate (1), was readily prepared in high yield by the reaction of 1,2-benzisoxazol-3-ol (2) with diphenyl phosphorochloridate (3) in the presence of triethylamine in benzene.The reaction of the carboxylic acids with the amines in the presence of 1 was investigated by two procedures, a two-step method and a one-step procedure.Both methods gave the corresponding amides and esters in high yields under mild conditions, but the one-step procedure was found to be superior to the two-step procedure because of its simplicity and speed.Furthermore, the activating agent 1 was shown to be a useful peptide forming reagent.

3,3'-(Phenylphosphinylidene)bis and 3,3'-(Phenylphosphinylidene)bis. New Activating Agents

New activating agents, 3,3'-(phenylphophinylidene)bis (4) and 3,3'-(phenylphosphinylidene)bis (5), were readily prepared by the reaction of phenylphosphonic dichloride (3) with 2(3H)-benzoxazolone (1) and 2(3H)-benzothiazolone (2) respectively in the presence of triethylamine at room temperature.The new activating agents 4 and 5 were found to be useful for the preparation of amides, esters, and dipeptides under mild conditions.Furthemore, the direct polycondensation of isophthalic acid with aromatic diamines using the activating agent 4 in the presence of pyridine proceeded fast at room temperature to produce polyamides with inherent viscosities up to 0.80 dL/g.