16653-19-3

Usage

InChI:InChI=1/C15H11NO3/c17-14-12-8-4-5-9-13(12)15(18)16(14)19-10-11-6-2-1-3-7-11/h1-9H,10H2

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 100-39-0 benzyl bromide 
• 201230-82-2 carbon monoxide 
• 3532-25-0 N-benzyloxy benzamide 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 98-88-4 benzoyl chloride 
• 85-44-9 phthalic anhydride 
• 622-33-3 N-benzyloxyamine 
• 17698-09-8 2-[(hydroxyamino)carbonyl]benzoic acid 
• 108-88-3 toluene 
• 100-51-6 benzyl alcohol 
• 100-44-7 benzyl chloride 

Downstream Products

• 524-38-9 N-hydroxyphthalimide 
• 622-33-3 N-benzyloxyamine 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 100-51-6 benzyl alcohol 
• 309756-04-5 2,3-dihydro-3-hydroxy-2-(benzoyloxy)-1H-isoindol-1-one 
• 867168-84-1 2-amino-3-hydroxy-propionaldehyde O-benzyl-oxime 

Relevant academic research and scientific papers

First discovery of novel 3-hydroxy-quinazoline-2,4(1H,3H)-diones as specific anti-vaccinia and adenovirus agents via ‘privileged scaffold’ refining approach

A series of 1,2,3-triazolyl 3-hydroxy-quinazoline-2,4(1H,3H)-diones was constructed utilizing Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) method. The biological significance of the novel synthesized quinazolines was highlighted by evaluating them in vitro for antiviral activity, wherein several compounds exhibited excellent activity specifically against vaccinia and adenovirus. Especially, 24b11 displayed the most potent inhibitory activity against vaccinia with an EC50value of 1.7 μM, which was 15 fold than that of the reference drug Cidofovir (EC50= 25 μM). 24b13 was the most potent compound against adenovirus-2 with an EC50value of 6.2 μM, which proved lower than all the reference drugs. Preliminary structure–activity relationships were also discussed. To the best of our knowledge, no data are present in the literature on antiviral activity of 3-hydroxy-quinazoline-2,4(1H,3H)-diones against DNA-viruses. Thus, these findings warrant further investigations (library expansion and compound refinement) on this novel class of antiviral agents.

A convenient large scale synthesis of O-benzylhydroxylamine

Synthetically useful O-benzylhydroxylamine can be conveniently prepared in large scale by reaction of N-hydroxyphthalimide and benzyl chloride in phase transfer conditions, followed by acidic hydrolysis of N-benzyloxyphthalimide. The overall yield is over 65%.

Improved synthesis of N-alkoxyphthalimides

Synthetically useful N-alkoxyphthalimide derivatives can be conveniently prepared in high yields from the reactions of N-hydroxyphthalimide with alkyl halides by using DBU in DMF.

Oxidative coupling of N-hydroxyphthalimide with toluene

Oxidative C-O-coupling of N-hydroxyphthalimide (NHPI) with toluene was studied. The reaction occurred in different organic solvents with a wide range of oxidants, such as (NH4)2Ce(NO3)6, PhI(OAc)2, KMnO4, Mn(OAc)3·2H2O, Pb(OAc)4, and Co(OAc)2/O2, to afford N-benzyloxyphthalimide in yield of 11-75%. Phthalimide-N-oxyl radicals, generated under the reaction conditions, could eliminate the hydrogen atom from the benzyl fragment of alkylarene at room temperature. Probably, formation of the product of the oxidative coupling occurred via recombination of benzyl and phthalimide-N-oxyl radicals.

Oxime ether heterocyclic formamide derivatives and preparation method and application thereof

The invention provides an oxime ether heterocyclic formamide derivative and a preparation method and application thereof, and particularly relates to the oxime ether heterocyclic formamide derivativeof which the chemical structural general formula is shown in a formula I. The invention discloses the structural general formula, a synthesis method and an application of the oxime ether heterocyclicformamide derivative serving as an insecticide, a bactericide and a plant virus resisting agent. The invention also discloses an application of the insecticidal composition in preventing and treatingagricultural, forestry and horticultural plant insect pests, diseases and virus diseases in combination with agriculturally acceptable auxiliaries or synergists and commercial insecticides, bactericides, plant virus resisting agents and acaricides, and a preparation method of the insecticidal composition in prevention and treatment of agricultural, forestry and horticultural plant insect pests, diseases and virus diseases.

Electrochemical access to benzimidazolone and quinazolinone derivatives: Via in situ generation of isocyanates

Isocyanates are the key intermediates for several organic transformations towards the synthesis of diverse pharmaceutical targets. Herein, we report the development of an oxidant-free protocol for electrochemical in situ generation of isocyanates. This strategy highlights expedient access to benzimidazolones and quinazolinones and eliminates the need for exogenous oxidants. Furthermore, detailed mechanistic studies provide strong support towards our hypothesis of in situ isocyanate generation. This journal is

Vinylogous Aza-Michael Addition of Urea Derivatives with p-Quinone Methides Followed by Oxidative Dearomative Cyclization: Approach to Spiroimidazolidinone Derivatives

Herein, we report an efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides (p-QMs) and dialkyloxy ureas under mild conditions. The strategy follows a two-step process involving an initial vinylogous conjugate addition of urea derivatives to p-QMs, followed by oxidative dearomative cyclization of open-chain product to the projected spiro-imidazolidinones. This protocol exhibits good functional group tolerance and provides a straightforward method to access spiro-imidazolidinone-cyclohexadienones. In follow-up chemistry, we have shown the debenzylation of spiroimidazolidinones to give N-hydroxycyclic ureas. (Figure presented.).

N-(benzyloxy)-2-chloronicotinamide compound as well as preparation method and application thereof

The invention belongs to the technical field of chemical synthesis and medicine application, and particularly relates to preparation and application of an N-(benzyloxy)-2-chloronicotinamide compound. The preparation method comprises the following steps: reacting phthalic anhydride with hydroxylamine, then reacting with triethylamine for acidification to prepare N-hydroxyphthalimide, then carrying out substitution and hydrazinolysis, and finally reacting with dichloronicotinoyl chloride to prepare the N-(benzyloxy)-2-chloronicotinamide compound. The preparation method disclosed by the invention is simple and convenient to operate, the structure of the obtained product is confirmed by a nuclear magnetic hydrogen spectrum, herbicidal activity tests are carried out on the obtained 15 target products, and results show that all target compounds have an obvious inhibition effect on the seeds of the Agrostis matsumurae under the concentration of 1mM, and the inhibition effect reaches 100%; and along with the decrease of the concentration, even if the concentration reaches 100 [mu] M, the target compound can still show good herbicidal activity.

Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains

Infections caused due to multidrug resistant organisms have emerged as a constant menace to human health. Even though numerous antibiotics are currently available for treating infectious diseases, a great number of bacterial strains have acquired resistance to many of them. Among these, infections caused due to Staphylococcus aureus are predominant in adult and paediatric population. Indole is a prominent chemical scaffold found in many pharmacologically active natural products and synthetic drugs. A number of oxime ether containing compounds have attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among all, compound 5h was found to possess potent activity against susceptible as well as MRSA and VRSA strains of S. aureus with MIC of 1 μg/mL and 2–4 μg/mL respectively. In addition, compound 5h was found to be non-toxic to Vero cells and exhibited good selectivity index of >40. Further, 5h, E-9a and E-9b possessed good biofilm inhibition against S. aureus. With these assuring biological properties, synthesized compounds could be potential prospective antimicrobial agents.

Synthesis, Crystal Structure, Herbicidal Activity, and SAR Study of Novel N-(Arylmethoxy)-2-chloronicotinamides Derived from Nicotinic Acid

Nicotinic acid, also known as niacin, is a natural product, which is widely found in plants and animals. To discover novel natural-product-based herbicides, a series of N-(arylmethoxy)-2-chloronicotinamides were designed and synthesized. Some of the new N-(arylmethoxy)-2-chloronicotinamides exhibited excellent herbicidal activity against Agrostis stolonifera (bentgrass) at 100 μM. Compound 5f (2-chloro-N-((3,4-dichlorobenzyl)oxy)nicotinamide) possessed excellent herbicidal activity against Lemna paucicostata (duckweed), with an IC50 value of 7.8 μM, whereas the commercial herbicides clomazone and propanil had values of 125 and 2 μM, respectively. The structure-activity relationships reported in this paper could be used for the development of new herbicides against monocotyledonous weeds.