The 3-(4-(Benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine

被引：0

作者：

Doherty, Katrina E. ^{[1
]}

Sandoval, Arturo Leon ^{[1
]}

Mercier, Ethan T. ^{[1
]}

Leadbeater, Nicholas E. ^{[1
]}

机构：

[1] Univ Connecticut, Dept Chem, 55 North Eagleville Rd, Storrs, CT 06269 USA

来源：

MOLBANK | 2023年 / 2023卷 / 03期

关键词：

oxidation; triazolopyridine; ring closure; sodium hypochlorite; green chemistry; OXIDATIVE CYCLIZATION; EFFICIENT SYNTHESIS; TRIAZOLOPYRIDINES; 1,2,4-TRIAZOLES; ALDEHYDES;

D O I：

10.3390/M1694

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [1,2,4]triazolo[4,3-a]pyridine derivative 3-(4-(benzyloxy)-3-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine was prepared in a 73% isolated yield by means of an oxidative ring closure of a hydrazine intermediate. Sodium hypochlorite was used as the oxidant and ethanol as a solvent, making the process a clean, green approach. The reaction was performed at room temperature for 3 h, and then the heterocycle was isolated in an analytically pure form by extraction, followed by passing the crude product mixture through a small plug of alumina.

引用

页数：5

共 24 条

[1] A convenient one-pot synthesis of N-fused 1,2,4-triazoles via oxidative cyclization using chromium (VI) oxide [J].

Bhatt, Ashish ;

Singh, Rajesh K. ;

Kant, Ravi .

SYNTHETIC COMMUNICATIONS, 2019, 49 (01) :22-31

[2] Facile one pot synthesis of N-fused 1,2,4-triazoles via oxidative cyclisation using DDQ [J].

Bhatt, Ashish ;

Singh, Rajesh K. ;

Kant, Ravi .

ARKIVOC, 2018, :236-247

[3] Properties of a triazolopyridine system as a molecular chemosensor for metal ions, anions, and amino acids [J].

Chadlaoui, Mimoun ;

Abarca, Belen ;

Ballesteros, Rafael ;

Ramirez de Arellano, Carmen ;

Aguilar, Juan ;

Aucejo, Ricardo ;

Garcia-Espana, Enrique .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24) :9030-9034

[4] Design, Synthesis, Activity Evaluation and Molecular Docking Study of Novel Janus kinase Inhibitors [J].

Du, Wenjun ;

Zhang, Fuli ;

Yan, Pei ;

Lai, Qingfu ;

Li, Junjian ;

Zhu, Daqian ;

Ye, Lianbao .

CHEMISTRYSELECT, 2021, 6 (17) :4212-4216

[5] BODIPY-Based Fluorescent Probes for Selective Visualization of Endogenous Hypochlorous Acid in Living Cells via Triazolopyridine Formation [J].

Hiranmartsuwan, Peraya ;

Wangngae, Sirilak ;

Nootem, Jukkrit ;

Kamkaew, Anyanee ;

Daengngern, Rathawat ;

Wattanathana, Worawat ;

Chansaenpak, Kantapat .

BIOSENSORS-BASEL, 2022, 12 (11)

[6] I2-TBHP-catalyzed one-pot highly efficient synthesis of 4,3-fused 1,2,4-triazoles from N-tosylhydrazones and aromatic N-heterocycles via intermolecular formal 1,3-dipolar cycloaddition [J].

Inturi, Surendra Babu ;

Kalita, Biswajit ;

Ahamed, A. Jafar .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (47) :11061-11064

[7] The chemistry of the triazolopyridines: an update [J].

Jones, G .

ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 83, 2002, 83 :1-70

[8] Current Status of Novel Pyridine Fused Derivatives as Anticancer Agents: An Insight into Future Perspectives and Structure Activity Relationship (SAR) [J].

Manaithiya, Ajay ;

Alam, Ozair ;

Sharma, Vrinda ;

Naim, Mohd. Javed ;

Mittal, Shruti ;

Azam, Faizul ;

Husain, Asif ;

Sheikh, Aadil Ahmad ;

Imran, Mohd. ;

Khan, Imran A. .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2021, 21 (25) :2292-2349

[9] A review of synthetic methods of 1,2,4-triazolopyridines and their therapeutic properties [J].

Melal, S. Poormoradkhan ;

Mahmoodi, N. O. .

RESULTS IN CHEMISTRY, 2023, 5

[10] Triazolopyridines as Selective JAK1 Inhibitors: From Hit Identification to GLPG0634 [J].

Menet, Christel J. ;

Fletcher, Stephen R. ;

Van Lommen, Guy ;

Geney, Raphael ;

Blanc, Javier ;

Smits, Koen ;

Jouannigot, Nolwenn ;

Deprez, Pierre ;

van der Aar, Ellen M. ;

Clement-Lacroix, Philippe ;

Lepescheux, Lien ;

Galien, Rene ;

Vayssiere, Beatrice ;

Nelles, Luc ;

Christophe, Thierry ;

Brys, Reginald ;

Uhring, Muriel ;

Ciesieski, Fabrice ;

Van Rompaey, Luc .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (22) :9323-9342

← 1 2 3 →