1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide to Thiocyanates: An Efficient and Eco-Friendly Synthesis of N -Aryl-2-((3-aryl-1,2,4-oxadiazol-5-yl)thio)acetamides

被引：2

作者：

Radhakrishna, Vamshikrishna Y. ^{[1
]}

Khatik, Gopal L. ^{[2
]}

Nair, Vipin A. ^{[3
]}

机构：

[1] REVA Univ, Dept Chem, Bangalore 560064, Karnataka, India

[2] Natl Inst Pharmaceut Educ & Res, Dept Med Chem, Raebareli 226002, Uttar Pradesh, India

[3] Amrita Vishwa Vidyapeetham, Sch Biotechnol, Amritapuri Campus, Kollam 690525, Kerala, India

来源：

SYNTHESIS-STUTTGART | 2024年 / 56卷 / 20期

关键词：

1,3-dipolar cycloaddition; N; -phenyl-2-thiocyanatoacetamide; N -hydroxybenzimidoyl chloride; 1,2,4-oxadiazole; triethylamine; nitrile oxide; ONE-POT SYNTHESIS; FACILE SYNTHESIS; 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES; ARYL THIOCYANATES; DESIGN; DERIVATIVES; AMIDOXIMES; DISCOVERY; ROUTE; AMIDE;

D O I：

10.1055/s-0043-1775390

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and eco-friendly procedure was developed for the synthesis of N -aryl-2-((3-aryl-1,2,4-oxadiazol-5-yl)thio)acetamides from N -aryl-2-thiocyanatoacetamides and substituted N -hydroxybenzimidoyl chlorides that were prepared easily from the commercially available anilines and aryl aldehydes, respectively. The N -aryl-2-thiocyanatoacetamide acts as a dipolarophile while the nitrile oxide formed in situ from substituted N -hydroxybenzimidoyl chloride acts as the nucleophilic partner in a 1,3-dipolar cycloaddition reaction mediated by triethylamine base in ethanol medium. The procedure affords excellent yields of desired products containing electron-withdrawing and electron-donating groups on the aromatic rings, in short reaction time with ease of operation. The procedure for the synthesis of scaffolds that are potentially valuable for their biological properties also offers the possibility of scale-up to higher quantities.

引用

页码：3173 / 3180

页数：8

共 40 条

[1] A novel, one-pot, three-component synthesis of 1,2,4-oxadiazoles under microwave irradiation and solvent-free conditions [J].

Adib, Mehdi ;

Mahdavi, Mohammad ;

Mahmoodi, Niusha ;

Pirelahi, Hooshang ;

Bijanzadeh, Hamid Reza .

SYNLETT, 2006, (11) :1765-1767

[2] Beyond direct Nrf2 activation; reinvestigating 1,2,4-oxadiazole scaffold as a master key unlocking the antioxidant cellular machinery for cancer therapy [J].

Ayoup, Mohammed Salah ;

Abu-Serie, Marwa M. ;

Abdel-Hamid, Hamida ;

Teleb, Mohamed .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2021, 220

[3] Oxadiazoles in Medicinal Chemistry [J].

Bostrom, Jonas ;

Hogner, Anders ;

Llinas, Antonio ;

Wellner, Eric ;

Plowright, Alleyn T. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (05) :1817-1830

[4] 'One-pot' synthesis of chiral N-protected α-amino acid-derived 1,2,4-oxadiazoles [J].

Braga, AL ;

Lüdtke, DS ;

Alberto, EE ;

Dornelles, L ;

Filho, WAS ;

Corbellini, VA ;

Rosa, DM ;

Schwab, RS .

SYNTHESIS-STUTTGART, 2004, (10) :1589-1594

[5] Concise total synthesis of phidianidine A and B [J].

Buchanan, Jacob C. ;

Petersen, Brandon P. ;

Chamberland, Stephen .

TETRAHEDRON LETTERS, 2013, 54 (45) :6002-6004

[6] Design, synthesis and cytotoxic evaluation of a library of oxadiazole-containing hybrids [J].

Camacho, Cristian M. ;

Pizzio, Marianela G. ;

Roces, David L. ;

Boggian, Dora B. ;

Mata, Ernesto G. ;

Bellizzi, Yanina ;

Barrionuevo, Elizabeth ;

Blank, Viviana C. ;

Roguin, Leonor P. .

RSC ADVANCES, 2021, 11 (47) :29741-29751

[7] New 1,2,4-Oxadiazole Nortopsentin Derivatives with Cytotoxic Activity [J].

Cascioferro, Stella ;

Attanzio, Alessandro ;

Di Sarno, Veronica ;

Musella, Simona ;

Tesoriere, Luisa ;

Cirrincione, Girolamo ;

Diana, Patrizia ;

Parrino, Barbara .

MARINE DRUGS, 2019, 17 (01)

[8] On the reactivity of nitrosoimidazoles with acids (the Cusmano-Ruccia reaction): a continuous source of new ring-into-ring interconversion [J].

Cosimelli, Barbara ;

Frenna, Vincenzo ;

Rambaldi, Mirella ;

Severi, Elda ;

Spinelli, Domenico .

TETRAHEDRON LETTERS, 2014, 55 (08) :1488-1490

[9] A review on synthetic account of 1,2,4-oxadiazoles as anti-infective agents [J].

Dhameliya, Tejas M. ;

Chudasma, Shrddhaba J. ;

Patel, Tanvi M. ;

Dave, Bhavarth P. .

MOLECULAR DIVERSITY, 2022, 26 (05) :2967-2980

[10] Acid-promoted reaction of N-(cyanomethyl) amide with nitrosation reagent: Facile synthesis of 1,2,4-oxadiazole-3-carboxamide [J].

Du, Shaoqing ;

Li, Jin ;

Fu, Wen ;

Xu, Xiaoyong ;

Shao, Xusheng ;

Qian, Xuhong .

TETRAHEDRON LETTERS, 2021, 76

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