Month: February 2023

Copper-Mediated Radiofluorination of Aryl Pinacolboronate Esters: A Straightforward Protocol by Using Pyridinium Sulfonates was written by Antuganov, Dmitrii;Zykov, Michail;Timofeev, Vasilii;Timofeeva, Ksenija;Antuganova, Yulija;Orlovskaya, Victoriya;Fedorova, Olga;Krasikova, Raisa. And the article was included in European Journal of Organic Chemistry in 2019.Application of 936902-12-4 This article mentions the following:

Radiofluorination of arylboronic acids pinacol esters (arylBPin) mediated by copper triflate pyridine complex is one of the more promising synthetic approaches for the direct introduction of nucleophilic [¹⁸F]fluoride into non-activated arenes and heteroarenes. However, the application of this method to the production of positron emission tomog. (PET) radiotracers in automated synthesizers remains a challenging task. The choice of phase-transfer catalyst (PTC) and corresponding base used for the generation of reactive [¹⁸F]fluoride species has a profound impact on the efficiency of the ¹⁸F-fluorination process. Herein the authors report the development of a simple procedure involving trapping of the aqueous [¹⁸F]fluoride on a weak anion-exchange resin (WAX) and its release by elution with pyridinium sulfonate in di-Me acetamide. Obtained reactive [¹⁸F]fluoride was used as-is in a copper-catalyzed fluorination reaction employing pyridinium salt as both PTC and base. High radiochem. conversion rates (RCCs) achieved for a series of simple arylBPin substrates and 4-[¹⁸F]fluoro-D,L-phenylalanine demonstrate the efficiency of this novel ¹⁸F-processing approach. Notably, the proposed method obviates conventional azeotropic drying steps, solvents evaporation and/or changeover and can be implemented on com. automated synthesizers. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4Application of 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) 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. A number of marketed drugs are available having benzoxazole as core active moiety like, nonsteroidal anti-inflammatory drug (NSAID)—flunoxaprofen, benoxaprofen, antibiotic—calcimycin.Application of 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Formal Carbene C-H Bond Insertion in the Cu(I)-Catalyzed Reaction of Bis(trimethylsilyl)diazomethane with Benzoxazoles and Oxazoles was written by Wang, Shuai;Xu, Shuai;Yang, Cheng;Sun, Hanli;Wang, Jianbo. And the article was included in Organic Letters in 2019.Category: benzoxazole This article mentions the following:

A Cu(I)-catalyzed cross-coupling reaction of bis(trimethylsilyl)diazomethane and benzoxazoles/oxazoles is reported. A wide range of functional groups can be tolerated in this transformation. This reaction provides a new method to directly introduce a 1,1-bis(trimethylsilyl)methyl group into heteroaromatic C-H bonds. Subsequent transformations of 1,1-bis(trimethylsilyl)-methylated heteroaromatic compounds are also presented. In the experiment, the researchers used many compounds, for example, 5-Methoxybenzo[d]oxazole (cas: 132227-03-3Category: benzoxazole).

5-Methoxybenzo[d]oxazole (cas: 132227-03-3) belongs to benzoxazole derivatives. Benzoxazole derivatives have different biological activities. Due to its versatile biological properties, benzoxazole has been incorporated as an essential pharmacophore and substructure in many medicinal compounds.Category: benzoxazole

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

A density functional study on the efficiencies of 2-mercaptobenzoxazole and its derivatives as chelating agents in flotation processes was written by Yekeler, Meftuni;Yekeler, Huelya. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2006.Electric Literature of C8H7NOS This article mentions the following:

By using the d. functional theory (DFT), we calculated some properties such as the energies of HOMO orbitals and the at. charges which are related to the reactive behavior of 2-mercaptobenzoxazole (MBO) and its Me and methoxy derivatives The results of the calculations indicated that the efficiencies of MBO and its derivatives depend on the investigated parameters, and 2-mercaptobenzothiazole (MBT) is better than MBO as a collector agent. Electron donating groups at the 6-position of MBO provided the best efficiency for MBO mol. The introduction of the Me group to any position of the benzene ring makes also MBO more powerful chelating agent by increasing the at. charges on the N and S atoms. The theor. obtained results are consistent with the exptl. data reported in the literature. In the experiment, the researchers used many compounds, for example, 6-Methyl-1,3-benzoxazole-2-thiol (cas: 23417-29-0Electric Literature of C8H7NOS).

6-Methyl-1,3-benzoxazole-2-thiol (cas: 23417-29-0) belongs to benzoxazole derivatives. Benzoxazole nucleus is one of the most important heterocyclic compounds exhibiting remarkable pharmacological activities. It is found within the chemical structures of pharmaceutical drugs such as flunoxaprofen and tafamidis.Electric Literature of C8H7NOS

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Phosphine-Catalyzed Dearomative [3 + 2] Cycloaddition of Benzoxazoles with a Cyclopropenone was written by Wang, Xingben;Yu, Congjun;Atodiresei, Iuliana L.;Patureau, Frederic W.. And the article was included in Organic Letters in 2022.COA of Formula: C8H7NO2 This article mentions the following:

The triphenylphosphine catalyzed dearomative [3+2] cycloaddition of benzoxazoles I (R = H, F, Ph, Me, etc.; R¹ = H, Me, F, Cl, Br, Et; RR¹ = -CH=CH-CH=CH-; R² = H, Me, F, Cl) with 1,2-diphenylcyclopropenone II (Ar = Ph, 3-methylphenyl) were described. The reaction scope, mechanism and possible future applications of this rare organocatalyzed cycloaddition were discussed. In the experiment, the researchers used many compounds, for example, 5-Methoxybenzo[d]oxazole (cas: 132227-03-3COA of Formula: C8H7NO2).

5-Methoxybenzo[d]oxazole (cas: 132227-03-3) belongs to benzoxazole derivatives. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. Benzoxazoles are prominent in medicinal chemistry due to their wide spectrum of pharmacological activities such as anti-inflammatory, antimycobacterial, antihistamine.COA of Formula: C8H7NO2

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

A Facile C-H Insertion Strategy using Combination of HFIP and Isocyanides: Metal-Free Access to Azole Derivatives was written by Gujjarappa, Raghuram;Vodnala, Nagaraju;Reddy, Velma Ganga;Malakar, Chandi C.. And the article was included in Asian Journal of Organic Chemistry in 2020.Formula: C8H7NO2 This article mentions the following:

An efficient metal-free approach has been devised towards the synthesis of azoles via C-H insertion protocol. Various isocyanides were examined as effective C1-synthons. The HFIP plays crucial role as hydrogen source and promoter of the reaction in order to reveal the maximum efficacies to accomplish the transformation in high yields of the products with excellent functional group tolerance. The control experiment affirmed 83% of deuterium incorporation, when the reaction was performed using HFIP-d₂. In the experiment, the researchers used many compounds, for example, 5-Methoxybenzo[d]oxazole (cas: 132227-03-3Formula: C8H7NO2).

5-Methoxybenzo[d]oxazole (cas: 132227-03-3) belongs to benzoxazole derivatives. Although benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important. In the past years, numerous benzoxazole derivatives have been synthesised and evaluated for their biological potential.Formula: C8H7NO2

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Copper-catalyzed direct thiolation of azoles with aliphatic thiols was written by Zhou, An-Xi;Liu, Xue-Yuan;Yang, Ke;Zhao, Shu-Chun;Liang, Yong-Min. And the article was included in Organic & Biomolecular Chemistry in 2011.Reference of 132227-03-3 This article mentions the following:

Cu(ii)-catalyzed direct thiolation of azoles with thiols is described via intermol. C-S bond formation/C-H functionalization under oxidative conditions. Both aryl thiols and aliphatic thiols are used as coupling partners, and furnished the thiolation products in moderate to good yields. The reaction is compatible with a wide range of heterocycles including oxazole, thiazole, imidazole and oxadiazole. In the experiment, the researchers used many compounds, for example, 5-Methoxybenzo[d]oxazole (cas: 132227-03-3Reference of 132227-03-3).

5-Methoxybenzo[d]oxazole (cas: 132227-03-3) belongs to benzoxazole derivatives. Benzoxazole derivatives have different biological activities. The wide range in therapeutic potential of benzoxazole derivatives is related to the favourable interactions of the benzoxazole moiety with different protein targets.Reference of 132227-03-3

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Dipole moments of benzoxazolinethiones substituted in the nucleus was written by Granzhan, V. A.;Poznanskaya, N. L.;Shvetsov-Shilovskii, N. I.;Laktionova, S. K.. And the article was included in Zhurnal Fizicheskoi Khimii in 1974.SDS of cas: 23417-29-0 This article mentions the following:

Comparison of calculated and exptl. dipole moments (μ) of benzoxazolinethiones (I; R = H, 5-Cl, 6-Cl, 5-Me, 6-Me, 6-Br, 6-MeO) showed that in benzene and dioxane I exist in the thione form. Increasing the temperature from 20 to 80° had little effect on μ. In dioxane μ was higher than in benzene. In the experiment, the researchers used many compounds, for example, 6-Methyl-1,3-benzoxazole-2-thiol (cas: 23417-29-0SDS of cas: 23417-29-0).

6-Methyl-1,3-benzoxazole-2-thiol (cas: 23417-29-0) 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.SDS of cas: 23417-29-0

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Synthesis of N-aryl-2-aminobenzoxazoles from substituted benzoxazole-2-thiol and 2-chloro-N-arylacetamides in KOH-DMF system was written by Wang, Guang-cheng;Wang, Jing;Li, Lu-yao;Chen, Shan;Peng, Ya-ping;Xie, Zhen-zhen;Chen, Ming;Deng, Bin;Li, Wen-biao. And the article was included in Heterocycles in 2017.Product Details of 23417-29-0 This article mentions the following:

A simple and novel method for the synthesis of N-aryl-2-aminobenzoxazoles I [R¹ = H, 5-F, 6-Me, etc. ; R² = 4-Cl, 2,4-di-Me, 4-OPh, etc.] from substituted benzoxazole-2-thiols II and 2-chloro-N-arylacetamides R²C₆H₄NHC(O)CH₂Cl in KOH-DMF system has been developed. The present protocol provides an attractive approach to access various N-aryl-2-aminobenzoxazoles I in moderate to good yields without using transition metal catalyst under very mild reaction condition. In the experiment, the researchers used many compounds, for example, 6-Methyl-1,3-benzoxazole-2-thiol (cas: 23417-29-0Product Details of 23417-29-0).

6-Methyl-1,3-benzoxazole-2-thiol (cas: 23417-29-0) belongs to benzoxazole derivatives. Benzoxazole nucleus is one of the most important heterocyclic compounds exhibiting remarkable pharmacological activities. It is found within the chemical structures of pharmaceutical drugs such as flunoxaprofen and tafamidis.Product Details of 23417-29-0

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Synthesis and anticancer activity of glycol-bridged bis-benzimidazoles was written by El-Kihel, Abdellatif;Jebbari, Said;Ahbala, Mustapha;Ait, Houssine Sir;Schmitt, Florian;Gold, Madeleine;Bauchat, Patrick;Schobert, Rainer;Biersack, Bernhard. And the article was included in DJ Journal of Engineering Chemistry and Fuel in 2019.Electric Literature of C8H7NOS This article mentions the following:

A series of bis-benzimidazoles with polyglycol-sulfide linker I [R = H, Me, F, NO₂; R¹ = H, Me; X = S, O, NH, N-propargyl; n = 1, 2] was prepared and tested for their tumor cell growth inhibitory activities. Two derivatives I [R = R¹ = H, X = NH, n = 1; R = R¹ = H, X = NH, n = 2] showed significant growth inhibitory activities against 518A2 melanoma cells. In addition, these compounds were active against multidrug resistant KB-V1^Vbl cervix carcinoma cells (vinblastine-resistant cells with overexpressed P-gp transporter) and MCF-7^Topo breast carcinoma cells (topotecan-resistant cells with overexpressed BCRP transporter). Thus, valuable lead structures for the design of new anticancer drugs based on benzimidazole systems were identified that could overcome drug resistance. In the experiment, the researchers used many compounds, for example, 6-Methyl-1,3-benzoxazole-2-thiol (cas: 23417-29-0Electric Literature of C8H7NOS).

6-Methyl-1,3-benzoxazole-2-thiol (cas: 23417-29-0) 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.Electric Literature of C8H7NOS

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Fluorination-¹⁸F using tri-tert-butanol ammonium iodide as phase-transfer catalyst: an alternative minimalist approach was written by Shinde, Sandip S.;Bolik, Kim-Viktoria;Maschauer, Simone;Prante, Olaf. And the article was included in Pharmaceuticals in 2021.HPLC of Formula: 936902-12-4 This article mentions the following:

The ¹⁸F syntheses of tracers for positron emission tomog. (PET) typically require several steps, including extraction of [¹⁸F]fluoride from H_2[¹⁸O]O, elution, and drying, prior to nucleophilic substitution reaction, being a laborious and time-consuming process. The elution of [¹⁸F]fluoride is commonly achieved by phase transfer catalysts (PTC) in aqueous solution, which makes azeotropic drying indispensable. The ideal PTC is characterized by a slightly basic nature, its capacity to elute [¹⁸F]fluoride with anhydrous solvents, and its efficient complex formation with [¹⁸F]fluoride during subsequent labeling. Herein, we developed tri-(tert-butanol)-methylammonium iodide (TBMA-I), a quaternary ammonium salt serving as the PTC for ¹⁸F-fluorination reactions. The favorable elution efficiency of [¹⁸F]fluoride using TBMA-I was demonstrated with aprotic and protic solvents, maintaining high ¹⁸F-recoveries of 96-99%. ¹⁸F-labeling reactions using TBMA-I as PTC were studied with aliphatic 1,3-ditosylpropane and aryl pinacol boronate esters as precursors, providing ¹⁸F-labeled products in moderate-to-high radiochem. yields. TBMA-I revealed adequate properties for application to ¹⁸F-fluorination reactions and could be used for elution of [¹⁸F]fluoride with MeOH, omitting an addnl. base and azeotropic drying prior to ¹⁸F-labeling. We speculate that the tert-alc. functionality of TBMA-I promotes intermol. hydrogen bonding, which enhances the elution efficiency and stability of [¹⁸F]fluoride during nucleophilic ¹⁸F-fluorination. In the experiment, the researchers used many compounds, for example, 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4HPLC of Formula: 936902-12-4).

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]oxazole (cas: 936902-12-4) belongs to benzoxazole derivatives. Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity. Due to its versatile biological properties, benzoxazole has been incorporated as an essential pharmacophore and substructure in many medicinal compounds.HPLC of Formula: 936902-12-4

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem