156780-52-8

Usage

Structure

Five-membered aromatic ring with one oxygen and one nitrogen atom

Type

Oxazole derivative

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals, reagent and intermediate for organic synthesis

Electron density

Increased by the presence of a methoxy group on the phenyl ring, which can result in altered chemical reactivity and potential medicinal properties

Biological activities

Studied for antimicrobial, antitumor, and anti-inflammatory properties, making it of interest for further exploration in drug development and discovery.

Upstream product

• 288-42-6 oxazol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 609345-33-7 oxazol-2-ylzinc(II) chloride 
• 696-62-8 para-iodoanisole 
• 107-20-0 2-chloroethanal 
• 3424-93-9 4-methoxyphenylacetamide 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 1064706-48-4 2-(4-methoxyphenyl)-4,5-dihydro-5-diethylsulfonamideoxazole 
• 133950-90-0 N-(2,2-dimethoxy-ethyl)-4-methoxy-benzamide 

Downstream Products

• 17064-22-1 2-(4-methoxyphenyl)-5-phenyl oxazole 
• 1020264-26-9 2-(4-methoxyphenyl)-5-(3-nitrophenyl)oxazole 
• 1020264-22-5 2-(4-methoxyphenyl)-5-o-tolyloxazole 
• 118425-86-8 C₁₆H₁₂ClNO₂ 
• 1020264-28-1 1-{4-[2-(4-methoxyphenyl)oxazol-5-yl]phenyl}ethanone 
• 96907-66-3 2-(4-methoxyphenyl)-5-(4-methylphenyl)oxazole 
• 853656-44-7 5-(4-bromophenyl)-2-(4-methoxyphenyl)oxazole 
• 1020264-29-2 2-(4-methoxyphenyl)-5-naphthalen-1-yloxazole 
• 54867-73-1 2-(4-methoxyphenyl)-5-(4-methoxyphenyl)oxazole 
• 1020264-24-7 2-(4-methoxyphenyl)-5-(4-trifluoromethylphenyl)oxazole 
• 87150-13-8 4-(oxazol-5-yl)benzonitrile 
• 68535-56-8 p-(2-oxazolyl)-phenol 

Relevant academic research and scientific papers

Palladium- and copper-mediated direct C-2 arylation of azoles - Including free (NH)-imidazole, -benzimidazole and -indole - Under base-free and ligandless conditions

The first palladium- and copper-mediated C-2 arylations of thiazole, oxazole, N-methylimidazole and N-arylimidazoles, as well as of free (NH)-imidazole, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions are described. Complete selectivity has been achieved under these unprecedented conditions, which allow the use of substrates containing base-sensitive groups, such the NH groups of imidazole, benzimidazole or indole, without their prior protection. No N-arylation products were detected in the arylation of free (NH)-imidazole, -benzimidazole and -indole. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

An improved method for the palladium cross-coupling reaction of oxazol-2-ylzinc derivatives with aryl bromides

An improved and scalable procedure to couple ozaxole and thiazole to aryl halides has been demonstrated. The required organozinc reagents were prepared from the aryllithium and solid ZnCl2. These reagents have been successfully coupled to a variety of aryl bromides and aryl iodides in good to excellent yields.

Efficient and highly regioselective direct C-2 arylation of azoles, including free (NH)-imidazole, -benzimidazole and -indole, with aryl halides

The Pd- and Cu-mediated reaction of a large variety of π-electron sufficient heteroarenes, which include free (NH)-imidazoles, -benzimidazole and -indole, with aryl iodides under ligandless and base-free conditions provides regioselectively the required 2-arylheterocycle derivatives in high yields. 2-Aryl-1-phenyl-1H-imidazoles can also be prepared by a one-pot domino HALEX and Pd- and Cu-mediated arylation reactions of 1-phenyl-1H-imidazole with activated and unactivated aryl bromides under base-free and ligandless conditions. The protocol for the synthesis of 2-arylazoles involving the use of aryl iodides has been found to be suitable for the efficient preparation of three bioactive compounds and a key intermediate in the synthesis of a heparanase inhibitor.

VASCULAR ADHESION PROTEIN-1 (VAP-1) MODULATORS AND THERAPEUTIC USES THEREOF

Disclosed herein are small molecule Vascular Adhesion Protein- 1 (VAP-1) modulator compositions, pharmaceutical compositions, the use and preparation thereof.

Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts

Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C?H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C?H bond functionalization steps. The Ru-catalyzed C?H arylation of the aryl unit of 2-aryloxazoles is also described. (Figure presented.).

PdII-Catalyzed Regio- and Enantioselective Oxidative C?H/C?H Cross-Coupling Reaction between Ferrocenes and Azoles

Asymmetric C?H bond functionalization reaction is one of the most efficient and straightforward methods for the synthesis of optically active molecules. Herein we disclose an asymmetric C?H/C?H cross-coupling reaction of ferrocenes with azoles such as oxazoles and thiazoles. Palladium(II)/monoprotected amino acid (MPAA) catalytic system which exhibits excellent reactivity and regioselectivity for oxazoles and thiazoles. This method offers a powerful strategy for constructing planar chiral ferrocenes. Mechanistic studies suggest that the C?H bond cleavage of azoles is likely proceeding through a SEAr process and may not be a turnover limiting step.

Warming Up to Oxazole: Noncryogenic Oxazole Metalation and Negishi Coupling Development

This report details the development of several suitable noncryogenic metalation conditions for the synthesis of oxazole zincate. Subsequent rounds of high-throughput catalyst screening ultimately led to the identification of several suitable Pd sources th

Synthesis and biological activity of 5-(4-methoxyphenyl)-oxazole derivatives

5-(4′-Methoxyphenyl)-oxazole (MPO), originally reported as a synthetic compound, was isolated from fungal culture broth as an inhibitor of hatch and growth of Caenorhabditis elegans. Nineteen MPO derivatives were chemically synthesized, but showed no effect on C. elegans hatch and growth. These findings strongly suggested that the whole structure of MPO is essential for anti-C. elegans activity.

Regioselective functionalization of the oxazole scaffold using TMP-bases of Mg and Zn

A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl·LiCl or TMPZnCl·LiCl led to the corresponding magnesiated or zincated species which

Copper-catalyzed oxidative arylation of heteroarenes under mild conditions using dioxygen as the sole oxidant

Dioxy-gently does it! A new copper-catalyzed oxidative cross-coupling reaction between heteroarenes and arylboronic esters has been developed. Uniformly high yields are obtained by using dioxygen as the sole oxidant under mild conditions (see scheme). Copyright