349614-89-7

Upstream product

• 696-62-8 para-iodoanisole 
• 615-36-1 2-bromoaniline 
• 13939-06-5 molybdenum hexacarbonyl 
• 100-09-4 4-methoxybenzoic acid 
• 201230-82-2 carbon monoxide 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 3526-43-0 N-(4-methoxybenzyl)aniline 
• 18600-55-0 2-(4-methoxyphenyl)-4H-3,1-benzoxazin-4-one 
• 103517-57-3 N₁-(4-methoxybenzoyl)-1,2-benzenediamine 
• 7465-88-5 4-methoxy-N-phenylbenzamide 
• 312525-41-0 N-tert-butyl-2-(4-methoxybenzamido)benzamide 
• 1152-07-4 2-(4-methoxyphenyl)-3H-quinazolin-4-one 
• 6265-92-5 2-(4-methoxy-phenyl)-benzothiazole 
• 838-34-6 2-(p-methoxyphenyl)benzoxazole 
• 880883-63-6 N-(2-bromophenyl)-4-methoxybenzothioamide 

Relevant academic research and scientific papers

Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source

A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.

Novel and efficient heterogeneous polymer supported copper catalyst for synthesis of 2-substituted Benzoxazoles from 2-Haloanilides

A novel polymer supported copper complex is prepared by the immobilization of copper iodide on chemically modified polyacrylonitrile and its application in heterogeneous catalysis is described. The catalyst was prepared by easy method via synthetic modification of Polyacrylonitrile (PAN) using ethylene diamine followed by the complexation with CuI. After characterization, this complex was explored as a green and efficient heterogeneous catalyst for the synthesis of 2-benzoxazoles from 2-haloanilides. The reaction was performed without adding additional ligand and the catalyst shows activity over a broad range of substrates with quantitative product yields. The catalyst was easily recovered by simple filtration and reused successfully for further cycle.

Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation

A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed. Upon irradiation with visible light, substrates undergo dehalogenative cyclization to 2-aryl benzothiazoles with high efficiency and selectivity. This photocyclization exhibits a high tolerance to various functional groups, is applicable for the synthesis of 2-alkyl benzothiazoles, and is easy to set up for gram-scale reaction.

Synthesis, Reactivity, Functionalization, and ADMET Properties of Silicon-Containing Nitrogen Heterocycles

Silicon-containing compounds have been largely ignored in drug design and development, despite their potential to improve not only the potency but also the physicochemical and ADMET (absorption, distribution, metabolism, excretion, toxicity) properties of drug-like candidates because of the unique characteristics of silicon. This deficiency is in large part attributable to a lack of general methods for synthesizing diverse organosilicon structures. Accordingly, a new building block strategy has been developed that diverges from traditional approaches to incorporation of silicon into drug candidates. Flexible, multi-gram-scale syntheses of silicon-containing tetrahydroquinoline and tetrahydroisoquinoline building blocks are described, along with methods by which diversely functionalized silicon-containing nitrogen heterocycles can be rapidly built using common reactions optimized to accommodate the properties of silicon. Furthermore, to better clarify the liabilities and advantages of silicon incorporation, select compounds and their carbon analogues were challenged in ADMET-focused biological studies.

A comparative study of the catalytic activity of Co- and CoFe2O4-NPs in C-N and C-O bond formation: synthesis of benzimidazoles and benzoxazoles from o-haloanilides

Nanoparticles of cobalt ferrite (CoFe2O4-NPs) and pure cobalt (Co-NPs) were synthesized, and after characterization, their catalytic activities for dehalogenative intramolecular C-O and C-N bond formation reactions were investigated and compared. These inexpensive and efficient catalysts enabled creation of new methods for the synthesis of benzimidazoles and benzoxazoles in green media, with ligand-free and mild reaction conditions. All the reactions resulted in moderate to excellent yields under the optimized reaction conditions; however, the reactions using Co-NPs as the catalyst were completed in relatively shorter reaction times. Furthermore, analysis showed that the reusability of the two catalytic systems is approximately comparable.

Palladium-catalyzed carbonylative synthesis of benzoxazinones from N -(o -bromoaryl)amides using paraformaldehyde as the carbonyl source

Carbonylation reactions have been widely used in organic synthesis. However, the manipulation of toxic and pressurized carbon monoxide limited their applications in organic laboratories. The search for alternative carbonyl sources as an important method for carbonylative organic synthesis is spreading. Herein, a series of substituted benzoxazinones were synthesized from N-(o-bromoaryl)amides by palladium-catalyzed carbonylation with paraformaldehyde as the carbonyl source, which is inexpensive, stable, and easy to use. Notably, this is the first example of using paraformaldehyde as the CO source in palladium-catalyzed carbonylative synthesis of heterocycles.

Pd(OAc)2-catalyzed carbonylative coupling of aryl iodide with ortho-haloamines in water

The carbonylative cross coupling of aryl iodide with ortho-haloaniline to ortho-haloanilide using phosphine-free Pd(OAc)2 catalyst in water as a reaction medium has been studied. The present protocol facilitated the reaction of o-haloanilines with a wide variety of hindered and functionalized aryl iodides, affording good yields of the desired products. The protocol was also extended for the synthesis of benzoxazoles through cyclization of ortho-haloanilide using Cu(acac)2 catalyst. Taylor & Francis Group, LLC.

BENZTHIAZOLE INHIBITORS OF POLY(ADP-RIBOSE)POLYMERASE

Inhibitors of poly(ADP-ribose)polymerase having a structure of Formula (I), ways to make them and methods of treating patients using them are disclosed.

Palladium-catalysed multicomponent aminocarbonylation of aryl or heteroaryl halides with Mo(CO)6i and aryl- or heteroarylamines using conventional heating

Di(hetero)arylamides have been synthesized in short reaction times by palladium-catalysed multicomponent aminocarbonylation of either electron-deficient or electron-rich heteroaryl halides and p-iodoanisole with, several, arylamines bearing either electro

Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides

A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.