Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles

A one-pot iodine-catalyzed multicomponent reaction has been developed for the selective preparation of 5-amino-4-(arylselanyl)-1H-pyrazoles from a diverse array of benzoylacetonitriles, arylhydrazines and diaryl diselenides. The reactions were conducted in MeCN as solvent at reflux temperature under air. The methodology presents a large functional group tolerance to electron-deficient, electron-rich, and bulky substituents and gave the expected products in good to excellent yields. The synthesized 1,3-diphenyl-4-(phenylselanyl)-1H-pyrazol-5-amine was submitted to an oxidative dehydrogenative coupling to produce a diazo compound confirmed by X-ray analysis.

[1]  R. Aggarwal,et al.  5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines , 2018, Beilstein journal of organic chemistry.

[2]  L. Savegnago,et al.  Ultrasound‐Assisted Synthesis and Antioxidant Activity of 3‐Selanyl‐1 H‐indole and 3‐Selanylimidazo[1,2‐a]pyridine Derivatives , 2017 .

[3]  A. Bernardino,et al.  Recently reported biological activities of pyrazole compounds. , 2017, Bioorganic & medicinal chemistry.

[4]  Shamsuzzaman,et al.  Review: biologically active pyrazole derivatives , 2017 .

[5]  B. Bandgar,et al.  Synthesis of novel α,α-difluoro-β-hydroxycarbonyl pyrazole derivatives as antioxidant, anti-inflammatory and anticancer agents , 2016, Medicinal Chemistry Research.

[6]  A. L. Braga,et al.  Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-a]pyridines by Employing I2 /DMSO as the Catalytic Oxidation System. , 2016, Chemistry.

[7]  Metin Zora,et al.  One-pot synthesis of 4-(phenylselanyl)-substituted pyrazoles , 2016 .

[8]  Diego Alves,et al.  Direct Synthesis of 4‐Organylselanylpyrazoles by Copper‐ Catalyzed One‐Pot Cyclocondensation and CH Bond Selenylation Reactions , 2015 .

[9]  S. Tu,et al.  Metal-Free Iodine-Catalyzed Synthesis of Fully Substituted Pyrazoles and Its Sulphenylation. , 2015, The Journal of organic chemistry.

[10]  R. Jacob,et al.  Synthesis of 4-Arylselanylpyrazoles Through Cyclocondensation Reaction Using Glycerol as Solvent , 2015 .

[11]  Ping Wu,et al.  Brønsted Acid-Catalyzed Phenylselenenylation of Internal Olefins , 2015 .

[12]  Dong Liu,et al.  Iodine-catalyzed oxidative coupling reactions utilizing C - H and X - H as nucleophiles. , 2015, Chemistry, an Asian journal.

[13]  M. Iwaoka,et al.  Organoselenium Chemistry: Between Synthesis and Biochemistry , 2014 .

[14]  Guigen Li,et al.  Oxidative Dehydrogenative Couplings of Pyrazol-5-amines Selectively Forming Azopyrroles , 2014, The Journal of organic chemistry.

[15]  Victoria L. Paddock,et al.  Regiocontrolled synthesis of 3- and 5-aminopyrazoles, pyrazolo[3,4-d]pyrimidines, pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]quinolinones as MAPK inhibitors , 2013 .

[16]  K. Parang,et al.  Copper triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF6] ionic liquid and evaluation of their anticancer activities. , 2013, RSC advances.

[17]  S. Dan,et al.  Structure-activity relationships of hybrid annonaceous acetogenins: powerful growth inhibitory effects of their connecting groups between heterocycle and hydrophobic carbon chain bearing THF ring on human cancer cell lines. , 2013, European journal of medicinal chemistry.

[18]  Renchun Yang,et al.  Molecular iodine-catalyzed multicomponent reactions: an efficient catalyst for organic synthesis , 2013 .

[19]  S. Tu,et al.  Novel double [3 + 2 + 1] heteroannulation for forming unprecedented dipyrazolo-fused 2,6-naphthyridines. , 2013, Organic letters.

[20]  B. Nachtsheim,et al.  Iodine in Modern Oxidation Catalysis , 2013, Synthesis.

[21]  Vinod Kumar,et al.  Synthesis of some new 3,5-diamino-4-(4′-fluorophenylazo)-1-aryl/heteroarylpyrazoles as antimicrobial agents , 2012, Medicinal Chemistry Research.

[22]  V. Ananikov,et al.  Transition-metal-catalyzed C-S, C-Se, and C-Te bond formation via cross-coupling and atom-economic addition reactions. , 2011, Chemical reviews.

[23]  M. Tiecco,et al.  Synthesis of Selenium-Substituted Pyrroles and Pyrazol-3-ones. , 2009 .

[24]  Vinod Kumar,et al.  Synthesis and antibacterial activity of some new 1-heteroaryl-5-amino-4-phenyl-3-trifluoromethylpyrazoles. , 2005, European journal of medicinal chemistry.

[25]  L. Bagnoli,et al.  Phenylselenenyl sulfate induced cyclization of allylhydrazines. Synthesis of pyrazole derivatives , 1997 .