February 2023 | Page 8 of 12 | Heterocyclic Building Blocks-Benzoxazole

Zhao, Shen et al. published their research in Applied Catalysis, A: General in 2014 | CAS: 99586-31-9

2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9) belongs to benzoxazole derivatives. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. A number of marketed drugs are available having benzoxazole as core active moiety like, nonsteroidal anti-inflammatory drug (NSAID)—flunoxaprofen, benoxaprofen, antibiotic—calcimycin.Synthetic Route of C13H8BrNO

Tri-lacunary polyoxometalates of Na₈H[PW₉O₃₄] as heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation and the synthesis of benzoxazole derivatives was written by Zhao, Shen;Chen, Yang;Song, Yu-Fei. And the article was included in Applied Catalysis, A: General in 2014.Synthetic Route of C13H8BrNO This article mentions the following:

We reported for the first time the development of tri-lacunary polyoxometalates (POMs) of Na₈H[A-PW₉O₃₄]·7H₂O and Na₈H[B-PW₉O₃₄]·19H₂O (Na-A-PW₉ and Na-B-PW₉) as highly selective and efficient heterogeneous Lewis base catalysts for Knoevenagel condensation, cyanosilylation of various aldehydes and ketones and the synthesis of benzoxazole derivatives at 25° under mild conditions. Since both Na-A-PW₉ and Na-B-PW₉ display no characteristic porosity, it is proposed that the catalytic reactions proceed not only on the surface and interface, but also in the bulk phase. The catalysts can be easily recovered and reused for at least six times without obvious decrease of catalytic activities and the structures of the catalysts remain unchanged after recycling. The easy preparation, high efficiency, reusability of the heterogeneous catalysts of Na-A-PW₉ and Na-B-PW₉ exhibit great potential for further application. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9Synthetic Route of C13H8BrNO).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Gu, Lijun et al. published their research in European Journal of Organic Chemistry in 2014 | CAS: 99586-31-9

2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9) belongs to benzoxazole derivatives. Being a heterocyclic compound, benzoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as flunoxaprofen and tafamidis.Safety of 2-(3-Bromophenyl)benzo[d]oxazole

Synthesis of 2-Arylbenzoxazoles through Oxidation of C-H Bonds Adjacent to Oxygen Atoms was written by Gu, Lijun;Wang, Wei;Xiong, Yong;Huang, Xiangzhong;Li, Ganpeng. And the article was included in European Journal of Organic Chemistry in 2014.Safety of 2-(3-Bromophenyl)benzo[d]oxazole This article mentions the following:

A practical and simple synthesis of benzoxazoles from easily available substrates was developed. The protocol is triggered by an iron-catalyzed tandem oxidative process from simple ether derivatives In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9Safety of 2-(3-Bromophenyl)benzo[d]oxazole).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Pham, Phuc H. et al. published their research in Organic Letters in 2019 | CAS: 5676-58-4

2,5-Dimethylbenzoxazole (cas: 5676-58-4) belongs to benzoxazole derivatives. Being a heterocyclic compound, benzoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. A number of marketed drugs are available having benzoxazole as core active moiety like, nonsteroidal anti-inflammatory drug (NSAID)—flunoxaprofen, benoxaprofen, antibiotic—calcimycin.Safety of 2,5-Dimethylbenzoxazole

Homo- and Heteroannulation of sp³ C-H Bonds in Acetophenones for Divergent Synthesis of Thienothiazoles was written by Pham, Phuc H.;Nguyen, Khang X.;Pham, Hoai T. B.;Nguyen, Tung T.;Phan, Nam T. S.. And the article was included in Organic Letters in 2019.Safety of 2,5-Dimethylbenzoxazole This article mentions the following:

A synthesis of fused thieno[3,2-d]thiazoles I (R = H, Me, OMe, etc.) via direct functionalization of C(sp³)-H bonds in acetophenones was reported. The transformation is divergent to afford either 2-phenylbenzo[4,5]thieno[3,2-d]thiazoles or benzo[4,5]thieno[3,2-d]thiazol-2-yl(phenyl)methanones. Cross-coupling of acetophenones with C-H bonds in phenylacetic acids, methylazaarenes, and aldehydes was also feasible. Excellent tolerance of functionalities was observed This method marks a rare functionalization of C(sp³)-H bonds in acetophenones to obtain heterocycles in the absence of pre-functionalized oxime esters. In the experiment, the researchers used many compounds, for example, 2,5-Dimethylbenzoxazole (cas: 5676-58-4Safety of 2,5-Dimethylbenzoxazole).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Llinares, Jeanine et al. published their research in Canadian Journal of Chemistry in 1979 | CAS: 5676-58-4

2,5-Dimethylbenzoxazole (cas: 5676-58-4) belongs to benzoxazole derivatives. Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity. Benzoxazoles are prominent in medicinal chemistry due to their wide spectrum of pharmacological activities such as antiparkinson, inhibition of hepatitis C virus, 5-HT3 antagonistic effect.Formula: C9H9NO

Structure and reactivity of benzoxazoles: carbon-13 nuclear magnetic resonance study was written by Llinares, Jeanine;Galy, Jean Pierre;Faure, Robert;Vincent, Emile Jean;Elguero, Jose. And the article was included in Canadian Journal of Chemistry in 1979.Formula: C9H9NO This article mentions the following:

Thirty-four benzoxazoles, oxazole, and 10 o-aminophenols were studied by ¹³C NMR spectroscopy. All the signals are attributed to substituent effects. The structures of the products obtained by the nitration of benzoxazole were determined by ¹³C NMR. The shifts induced by substitution at the 2 position are discussed as a function of an empirical model by using the structural parameters F, R, and Q^*. Azido-tetrazole equilibrium (N₃ in position 2) and prototropic tautomerism (NH₂, OH, and SH in position 2) are also discussed. The chem. shifts and coupling constants of oxazole and unsubstituted benzoxazole are compared. In the experiment, the researchers used many compounds, for example, 2,5-Dimethylbenzoxazole (cas: 5676-58-4Formula: C9H9NO).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Shelkar, Radheshyam et al. published their research in Tetrahedron Letters in 2013 | CAS: 99586-31-9

2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9) belongs to benzoxazole derivatives. Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity. It is found within the chemical structures of pharmaceutical drugs such as flunoxaprofen and tafamidis.Electric Literature of C13H8BrNO

Nano ceria catalyzed synthesis of substituted benzimidazole, benzothiazole, and benzoxazole in aqueous media was written by Shelkar, Radheshyam;Sarode, Sachin;Nagarkar, Jayashree. And the article was included in Tetrahedron Letters in 2013.Electric Literature of C13H8BrNO This article mentions the following:

A series of substituted benzimidazoles, benzothiazoles, and benzoxazoles was synthesized by combining 1,2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, heteroaryl, aliphatic, α,β-unsaturated aldehydes in the presence of nano ceria (CeO₂) as an efficient heterogeneous catalyst. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9Electric Literature of C13H8BrNO).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Guo, Ying et al. published their research in Chemistry – An Asian Journal in 2021 | CAS: 99586-31-9

2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9) belongs to benzoxazole derivatives. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. Due to its versatile biological properties, benzoxazole has been incorporated as an essential pharmacophore and substructure in many medicinal compounds.Reference of 99586-31-9

A TEMPO-Functionalized Ordered Mesoporous Polymer as a Highly Active and Reusable Organocatalyst was written by Guo, Ying;Wang, Wei David;Li, Shengyu;Zhu, Yin;Wang, Xiaoyu;Liu, Xiao;Zhang, Yuan. And the article was included in Chemistry – An Asian Journal in 2021.Reference of 99586-31-9 This article mentions the following:

The properties of high stability, periodic porosity, and tunable nature of ordered mesoporous polymers make these materials ideal catalytic nanoreactors. However, their application in organocatalysis has been rarely explored. We report herein for the first time the incorporation of a versatile organocatalyst, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO), into the pores of an FDU-type mesoporous polymer via a pore surface engineering strategy. The resulting FDU-15-TEMPO possesses a highly ordered mesoporous organic framework and enhanced stability, and shows excellent catalytic activity in the selective oxidation of alcs. and aerobic oxidative synthesis of 2-substituted benzoxazoles, benzimidazoles and benzothiazoles. Moreover, the catalyst can be easily recovered and reused for up to 7 consecutive cycles. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9Reference of 99586-31-9).

2-(3-Bromophenyl)benzo[d]oxazole (cas: 99586-31-9) belongs to benzoxazole derivatives. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. Due to its versatile biological properties, benzoxazole has been incorporated as an essential pharmacophore and substructure in many medicinal compounds.Reference of 99586-31-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Lee, Jung June et al. published their research in Tetrahedron in 2009 | CAS: 5676-58-4

2,5-Dimethylbenzoxazole (cas: 5676-58-4) belongs to benzoxazole derivatives. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization. A number of marketed drugs are available having benzoxazole as core active moiety like, nonsteroidal anti-inflammatory drug (NSAID)—flunoxaprofen, benoxaprofen, antibiotic—calcimycin.HPLC of Formula: 5676-58-4

Indium-mediated one-pot synthesis of benzoxazoles or oxazoles from 2-nitrophenols or 1-aryl-2-nitroethanones was written by Lee, Jung June;Kim, Jihye;Jun, Young Moo;Lee, Byung Min;Kim, Byeong Hyo. And the article was included in Tetrahedron in 2009.HPLC of Formula: 5676-58-4 This article mentions the following:

One-pot reduction-triggered heterocyclizations from 2-nitrophenols to benzoxazoles and from 1-aryl-2-nitroethanones to oxazoles were investigated. In the presence of indium/AcOH in benzene at reflux, 2-nitrophenols and R-C(OMe)₃ (R=H, Me, Ph) produced excellent yields of corresponding benzoxazoles within an hour. Similarly, 1-aryl-2-nitroethanones and Ph-C(OMe)₃ in the presence of indium/AcOH in acetonitrile transformed into the corresponding oxazoles with good yields. In the experiment, the researchers used many compounds, for example, 2,5-Dimethylbenzoxazole (cas: 5676-58-4HPLC of Formula: 5676-58-4).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Kumar, Vishal et al. published their research in Tetrahedron in 2022 | CAS: 5676-58-4

2,5-Dimethylbenzoxazole (cas: 5676-58-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have gained a lot of importance in the past few years because of their use in intermediates for the preparation of new biological materials. Due to its versatile biological properties, benzoxazole has been incorporated as an essential pharmacophore and substructure in many medicinal compounds.Name: 2,5-Dimethylbenzoxazole

Metal-free direct annulation of 2-aminophenols and 2-aminothiophenols with unactivated amides through transamidation: Access to polysubstituted benzoxazole and benzothiazole derivatives was written by Kumar, Vishal;Dhawan, Sanjeev;Bala, Renu;Girase, Pankaj Sanjay;Singh, Parvesh;Karpoormath, Rajshekhar. And the article was included in Tetrahedron in 2022.Name: 2,5-Dimethylbenzoxazole This article mentions the following:

Simple yet novel oxidant, metal and solvent-free green protocol for synthesizing differently 2-substituted 1,3-benzoxazoles I [R¹ = Me, Ph, Bn, etc.; R² = H, 6-Me, 5-Cl, etc.; X = O] and benzothiazoles I [R¹ = Me; R² = H, 5-Cl; X = S] from 2-aminophenol hydrochloride salt, unactivated amide as in situ carbon source was reported. Further, the hydrogen ion of hydrochloride played a crucial role in amide activation followed nucleophilic attack that through eliminations of amine as a side product, and de-hydrolysis step leads to final annulation. This versatile strategy was applicable to a wide variety of differently substituted o-aminophenols, unactivated aliphatic and aromatic amides, yielding the corresponding product in good to excellent yields in a single step. In the experiment, the researchers used many compounds, for example, 2,5-Dimethylbenzoxazole (cas: 5676-58-4Name: 2,5-Dimethylbenzoxazole).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Kawahara, Norio et al. published their research in Heterocycles in 1981 | CAS: 5676-58-4

2,5-Dimethylbenzoxazole (cas: 5676-58-4) belongs to benzoxazole derivatives. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization. Due to its versatile biological properties, benzoxazole has been incorporated as an essential pharmacophore and substructure in many medicinal compounds.Reference of 5676-58-4

Some novel reactions of benzoxazole derivatives with dimethyl acetylenedicarboxylate. II was written by Kawahara, Norio;Katsuyama, Michiko;Itoh, Tsuneo;Ogura, Haruo. And the article was included in Heterocycles in 1981.Reference of 5676-58-4 This article mentions the following:

Reaction of 2-alkylbenzoxazoles I (R, R¹ = H, H; Me, H; Me, Me) with R²CCR² (R² = CO₂Me) in EtOH or CMe₃OH at room temperature gave tricyclic compound II, hydration product III (R³ = H), solvent adduct III (R³ = CMe₃), and ring-opened compounds RC₆H₃(O₂CCH₂R¹)NHCR²:CHR²-4,3 and RC₆H₃(OH)[N(COCH₂R¹)CR²:CHR²]-4,3 (IV). IV was a main product of photochem. reaction of I with R²CCR². In the experiment, the researchers used many compounds, for example, 2,5-Dimethylbenzoxazole (cas: 5676-58-4Reference of 5676-58-4).

2,5-Dimethylbenzoxazole (cas: 5676-58-4) belongs to benzoxazole derivatives. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization. Due to its versatile biological properties, benzoxazole has been incorporated as an essential pharmacophore and substructure in many medicinal compounds.Reference of 5676-58-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Graves, Brian M. et al. published their research in Scientific Reports in 2020 | CAS: 5676-58-4

2,5-Dimethylbenzoxazole (cas: 5676-58-4) belongs to benzoxazole derivatives. Benzoxazole derivatives have different biological activities. Benzoxazoles are prominent in medicinal chemistry due to their wide spectrum of pharmacological activities such as anti-inflammatory, antimycobacterial, antihistamine.Synthetic Route of C9H9NO

Comprehensive characterization of mainstream marijuana and tobacco smoke was written by Graves, Brian M.;Johnson, Tyler J.;Nishida, Robert T.;Dias, Ryan P.;Savareear, Benjamin;Harynuk, James J.;Kazemimanesh, Mohsen;Olfert, Jason S.;Boies, Adam M.. And the article was included in Scientific Reports in 2020.Synthetic Route of C9H9NO This article mentions the following:

Recent increases in marijuana use and legalization without adequate knowledge of the risks necessitate the characterization of the billions of nanoparticles contained in each puff of smoke. Tobacco smoke offers a benchmark given that it has been extensively studied. Tobacco and marijuana smoke particles are quant. similar in volatility, shape, d. and number concentration, albeit with differences in size, total mass and chem. composition Particles from marijuana smoke are on average 29% larger in mobility diameter than particles from tobacco smoke and contain 3.4 times more total mass. New measurements of semivolatile fractions determined that >97% of the mass and volume of the particles from either smoke source are comprised of semivolatile compounds For tobacco smoke and marijuana smoke, resp., 4350 and 2575 different compounds are detected, of which 670 and 536 (231 in common) are tentatively identified, and of these, 173 and 110 different compounds (69 in common) are known to cause neg. health effects through carcinogenic, mutagenic, teratogenic, or other toxic mechanisms. This study demonstrates striking similarities between marijuana and tobacco smoke in terms of their phys. and chem. properties. In the experiment, the researchers used many compounds, for example, 2,5-Dimethylbenzoxazole (cas: 5676-58-4Synthetic Route of C9H9NO).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem