Temperature-controlled S vs N selective alkylation of 1-phenyl tetrazole-5-thione with α,β-unsaturated systems in solvent-free organic salt media

References

• Salih BD, Alheety MA, Mahmood AR, et al. Hydrogen storage capacities of some new Hg (II) complexes containing 2-acetylethiophene. Inorg Chem Commun. 2019;103:100–106.
   Web of Science ®Google Scholar
• Hameed AA, Alheety MA, Mahmood AR, et al. H2 storage abilities of some novel Pd (II) complexes containing 2H [1, 4] benzothiazin-3 (4H)-one. Inorg Chem Commun. 2019;106:11–17.
   Web of Science ®Google Scholar
• Ulghafoor A-JS, Karadağ MA, Aydin A, et al. Synthesis, characterization and anti-tumor activity of Pd(II) complexes with 4,5-benzo-3H-1,2-dithiole-3-thione. Transition Met Chem. 2019;44:575–583.
   Web of Science ®Google Scholar
• dos Santos Chagas C, Fonseca FL, Mater IA. Quinoline-derivative coordination compounds as potential applications to antibacterial and antineoplasic drugs. Sci Eng. 2019;98:1043–1052.
   Google Scholar
• Al-Janabia ASM, Alheety MA, Al-Samrai OAY, et al. Anti-cancer and anti-fungal evaluation of novel palladium(II) 1-phenyl-1H-tetrazol-5-thiol complexes. Inorg Chem Commun. 2020;121:108193–108199.
   Web of Science ®Google Scholar
• Myznikov LV, Hrabalek A, Koldobskii GI. Drugs in the tetrazole series. Chem Heterocycl Compd. 2007;43:1–9.
   Google Scholar
• Katritzky AR, Ramsden CA, Scriven EFV, et al. Comprehensive heterocyclic chemistry III. Comp Heterocycl Chem. Eds. Oxford: Elsevier. 2008;3:257-271.
   Google Scholar
• Myznikov LV, Vorona SV, Artamonova TV, et al. Tetrazoles with oxygen-, sulfur-, and selenium-containing substituents. Russ Chem Bull. 2016;65:923–938.
   Web of Science ®Google Scholar
• Myznikov LV, Vorona SV, Artamonova TV, et al. Mechanism of the zinc-catalyzed addition of azide ion to unsaturated compounds: synthesis of 5-substituted 1H-tetrazoles from nitriles and of 1-substituted 1H-tetrazole-5-thiols from isothiocyanates. Russ J Gen Chem. 2017;87:731–738.
   Web of Science ®Google Scholar
• Ostrovskii VA, Trifonov RE, Popova EA. Medicinal chemistry of tetrazoles. Russ Chem Bull. 2012;61:768–780.
   Web of Science ®Google Scholar
• Singh H, Chawla AS, Kapoor VK, et al. Medicinal chemistry of tetrazoles. Prog Med Chem. 1980;17:151–183.
   PubMedGoogle Scholar
• Bourdonnec BL, Bourdonnec ME, Yous S, et al. Synthesis and pharmacological evaluation of new pyrazolidine-3,5-diones as AT1 angiotensin II receptor antagonists. J Med Chem. 2000;43:2685–2697.
   PubMed Web of Science ®Google Scholar
• Tremblay LW, Xu H, Blanchard JS. Structures of the Michaelis-complex (1.2 Å) and the covalent acyl-intermediate (2.0 Å) of cefamandole bound in the active sites of the mycobacterium tuberculosis β-lactamase K73A and E166A mutants. Biochemistry. 2010;49:9685–9687.
   PubMed Web of Science ®Google Scholar
• Diwakar SD, Bhagwat SS, Shingare MS, et al. Substituted 3-((Z)-2-(4-nitrophenyl)-2-(1H-tetrazol-5-yl) vinyl)-4H-chromen-4-ones as novel anti-MRSA agents: synthesis, SAR, and in-vitro assessment. Bioorg Med Chem Lett. 2008;18:4678–4681.
   PubMed Web of Science ®Google Scholar
• Rajasekaran A, Thampi PP. Synthesis and analgesic evaluation of some 5-[beta-(10-phenothiazinyl)ethyl]-1-(acyl)-1,2,3,4-tetrazoles. Eur J Med Chem. 2004;39:273–279.
   PubMed Web of Science ®Google Scholar
• Kumar CNSSP, Parida DK, Santhoshi A, et al. Synthesis and biological evaluation of tetrazole containing compounds as possible anticancer agents. Med Chem Commun. 2011;2:486–492.
   Web of Science ®Google Scholar
• Ichikawa T, Kitazaki T, Matsushita Y, et al. Optically active antifungal azoles. XII. synthesis and antifungal activity of the water-solubleprodrugs of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazole-1-yl)-propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone. Chem Pharm Bull. 2001;49:1102–1109.
   PubMed Web of Science ®Google Scholar
• Morjan RY, Al-Attar NH, Abu-Teim OS, et al. Synthesis, antibacterial and QSAR evaluation of 5-oxo and 5-thio derivatives of 1,4-disubstituted tetrazoles. Bioorg Med Chem Lett. 2015;25:4024–4028.
   PubMed Web of Science ®Google Scholar
• Luo YP, Yang GF. Discovery of a new insecticide lead by optimizing a target-diverse scaffold: tetrazolinone derivatives. Bioorg Med Chem. 2007;15:1716–1724.
   PubMed Web of Science ®Google Scholar
• Foldenyi R. Neue 1H-tetrazol-5-thiol-derivate als pestizide, 2. Mitt. cyanimidodithiokohlensäureester. Monatsh Chem. 1995;126:1035–1043.
   Google Scholar
• Andres-Gil JI, Alcazar-Vaca MJ, Pastor-Fernandez J, et al. EP 56951 2006067139. 2006.
   Google Scholar
• Show-Reid CA, Miller MD, Hazuda DJ, et al. US 16671 2005115147. 2005.
   Google Scholar
• Cirino G, Mirone V, Ignarro LJ, et al. EP 50779 2004043443. 2004.
   Google Scholar
• Janssens FE, Sommen FM, Surleraux DLNG, et al. EP 4660 9716440. 1997.
   Google Scholar
• Shih TL, Candelore MR, Cascieri MA, et al. L-770,644: A potent and selective human β3 adrenergic receptor agonist with improved oral bioavailability. Bioorg Med Chem Lett. 1999;9:1251–1254.
   PubMed Web of Science ®Google Scholar
• Shenk T, Rabinowitz JD, Munger J, et al. US 6959 2009023059. 2009.
   Google Scholar
• Kang HY, Koh HY, Kim HM, Yoon D, Chang MH. Synthesis and biological evaluation of new aminothiazolyl cephalosporins with elongated side chains. Korean J Med Chem. 1991;1:18–25.
   Google Scholar
• Sindkhedkar MD, Bhavsar SB, Patil VJ, et al. IN 208 2007023507. 2007.
   Google Scholar
• Dunlap RP, Boaz NW, Mura AJ, et al. US 2434 9013549. 1990.
   Google Scholar
• Fujimoto M, Maeda T, Okumura K, et al. Process development and pilot-scale synthesis of cefotetan. Org Process Res Dev. 2004;8:915–919.
   Web of Science ®Google Scholar
• Carmine AA, Brogden RN, Heel RC, et al. Moxalactam (latamoxef). Drugs. 1983;26:279–333.
   PubMed Web of Science ®Google Scholar
• Yoon J, Kwack WG, Shim WS, et al. Quantitation of plasma and biliary cefpiramide concentrations in human samples using high-performance liquid chromatography. Biomed Chromatogr. 2020;34:49–57.
   Web of Science ®Google Scholar
• Kaiser GV, Gorman M, Webber JA. Cefamandole-a review of chemistry and microbiology. J Infect Dis. 1978;137:S10–S16.
   PubMed Web of Science ®Google Scholar
• Karabanovich G, Roh J, Smutný T, et al. 1-Substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their isosteric analogs: A new class of selective antitubercular agents active against drug-susceptible and multidrug-resistant mycobacteria. Eur J Med Chem. 2014;82:324–340.
   PubMed Web of Science ®Google Scholar
• Chen XZ, Xu P, Liu L, et al. Synthesis and antibacterial activity of novel ketolides with 11,12-sulfur contained aryl alkyl side chains. Eur J Med Chem. 2011;46:208–217.
   PubMed Web of Science ®Google Scholar
• Meyer-Rochow VB, Lindstrom M. Electrophysiological and histological observations on the eye of adult, female Diastylis rathkei (Crustacea, Malacostraca, Cumacea). Biol Bull. 1988;175:144–153.
   Web of Science ®Google Scholar
• Whitcomb DR, Chen S, Shore JD, et al. Optical properties of nanoparticulate metallic silver in photothermographic imaging materials. J Imaging Sci Technol. 2005;49:370–380.
   Web of Science ®Google Scholar
• Sattar Irzoqi AA, Al-Janabi ASM, Jirjes HM. Synthesis and characterization of phthalimide-benzothiazole mercury(II) complexes with diphosphine and diamines. Diyala J Pure Sci. 2017;13:1–11.
   Google Scholar
• Moderhack D. Ring transformations in tetrazole chemistry. J Prakt Chem. 1998;340:687–709.
   Google Scholar
• Al-Janabi AS, Ahmed SA. Cadmium(II) complexes containing the mixed ligands benz-1,3-imidazoline -2-thione, benz-1,3-oxazoline -2-thione, benz-1,3-thiazoline -2-thione, and diphosphine Ph2P(CH2)nPPh2, n = 1-4 or triphenyl phosphine. Orient J Chem. 2011;27:1563–1571.
   Google Scholar
• Bharty MK, Dani RK, Kushawaha SK, et al. Mn(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II) and Co(II) complexes of 1-phenyl-1H-tetrazole-5-thiol: synthesis, spectral, structural characterization and thermal studies. Polyhedron. 2015;88:208–221.
   Web of Science ®Google Scholar
• Koldobskii GI, Hrabalek A, Esikov KA. 1-Substituted 5-alkyl(aryl)sulfanyltetrazoles and their derivatives. Russ J Org Chem. 2004;40:447–461.
   Web of Science ®Google Scholar
• Ostrovskii VA, Koldobskii GI, Trifonov RE. Tetrazoles. Comp Heterocycl Chem III. 2008;6:257–423.
   Google Scholar
• Waisser K, Vansura J, Hrabalek A, et al. Antimycobacterial derivatives of tetrazole. Coll Czech Chem Commun. 1991;56:2389–2394.
   Google Scholar
• Blakemore PR. The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compounds. J Chem Soc Perkin Trans. 2002;23:2563–2585.
   Google Scholar
• Elguero J, Marzin C, Katritzky AR, et al. The tautomerism of heterocycles. New York: Academic; 1976.
   Google Scholar
• Bojarska-Olejnik E, Stefaniak L, Witanowski M, et al. A 15N NMR study of the tautomeric equilibria of some 5-substituted tetrazoles. Bull Chem Soc Jpn. 1986;59:3263–3265.
   Web of Science ®Google Scholar
• Poplavskaya YV, Trifonov RE, Shcherbinin MB, et al. Quantum-chemical study of five-membered nitrogen-containing heterocycles: III. Prototropic tautomerism of 1-aryltetrazol-5-ones and 1-aryltetrazole-5-thiones. Russ J Org Chem. 2000;36:1788–1792.
   Web of Science ®Google Scholar
• Labbe G, Vermeulen G, Flemal J, et al. Synthesis of 1,4-disubstituted tetrazoline-5-thiones. J Org Chem. 1976;41:1875–1876.
   Web of Science ®Google Scholar
• Zweifel T, Nielsen M, Overgaard J, et al. Practical synthesis of β-carbonyl phenyltetrazolesulfones and investigations of their reactivities in organocatalysis. Eur J Org Chem. 2011;1:47–52.
   Google Scholar
• Aleshunin PA, Aleshunina DV, Ostrovskii VA. New method of 5-mercaptotetrazoles functionalization. Russ J Org Chem. 2011;47:1786–1788.
   Web of Science ®Google Scholar
• Montazerozohori M, Joohari S, Karami B, et al. Fast and highly efficient solid state oxidation of thiols. Molecules. 2007;12:694–702.
   PubMed Web of Science ®Google Scholar
• Fathalla W, Ali IAI. Efficient synthesis of 1-substituted-4-phenyl-1, 4-dihydro-5H-tetrazole-5-thione and (1-phenyl-1H-tetrazol-5-yl)thioacetyl derivatives. Heteroat Chem. 2007;18:637–643.
   Web of Science ®Google Scholar
• Krutak JJ, Burpitt RD, Moore WH, et al. J Org Chem Res. 1979;44:3847–3858.
   Web of Science ®Google Scholar
• Hunig S, Oette KH. Azofarbstoffe durch oxydative kupplung, XVI. Synthesen kupplungsfähiger hydrazone aromatischer 5-ring-heterocyclen mit 2 bis 4 heteroatomen. Justus Liebigs Ann Chem. 1961;641:94–103.
   Google Scholar
• Nirenburg VL, Postovskii IY, Chertkova EI. Pyridylethylation of cyclic thioamides and amides. I. Pyridylethylation in the tetrazole and 1, 2, 4-triazole series. Izv Vyssh Uchebn Zaved Ser Khim Khim Tekhnol. 1965;8:258–261.
   Google Scholar
• Neidlein R, Tauber J. Tetrazolylmercaptomethyl-isocyanate und ihre Derivate. Chem Ber. 1967;100:736–740.
   Google Scholar
• Lippmann E, Reifegerste D. Alkylierungsreaktionen am 1-phenyl-5-mercaptotetrazol. Z Chem. 1975;15:54–55.
   Google Scholar
• Kocienski PJ, Bell A, Blakemore PR. 1-tert-butyl-1H-tetrazol-5-yl sulfones in the modified Julia olefination. Synlett. 2000: 365–366.
   Web of Science ®Google Scholar
• Alper H, Stout RW. Azole chemistry. VI.†. tetrazolo[5,4-b] [1,3] thiazinium salts. J Heterocycl Chem. 1973;10:569–574.
   Web of Science ®Google Scholar
• Bartels-Keith JR, Mahoney JB, Puttick AJ. Elimination reactions of alpha-substituted thymines derived from tautomeric heterocyclic thiols and selenols. J Org Chem. 1985;50:980–987.
   Web of Science ®Google Scholar
• Quast H, Nahr U. Photochemische stickstoff-eliminierung aus 1,4-dihydro-1-phenyl-5H-tetrazol-5-onen und -thionen. Benzimidazolone und carbodiimide. Chem Ber. 1985;118:526–540.
   Google Scholar
• Uchida M, Komatsu M, Morita S, et al. Studies on gastric antiulcer active agents. III.: synthesis of 1-substituted 4-(5-tetrazolyl) thio-1-butanones and related compounds. Chem Pharm Bull. 1989;37:958–961.
   PubMed Web of Science ®Google Scholar
• Waisser K, Kunes J, Hrabalek A, et al. New groups of potential antituberculotics: 5-alkylthio-1-aryltetrazoles. Collect Czech Chem Commun. 1996;61:791–798.
   Google Scholar
• Blakemore PR, Kocienski PJ, Morley A, et al. A synthesis of herboxidiene. J Chem Soc Perkin Trans. 1999;1:955–968.
   Google Scholar
• Compostella F, Franchini L, Panza L, et al. A formal synthesis of 3-O-(4-methoxybenzyl)-azidosphingosine by a modified Julia olefination. Tetrahedron. 2002;58:4425–4428.
   Web of Science ®Google Scholar
• Trost BM, Chisholm JD, Wrobleski ST, et al. Ruthenium-catalyzed alkene-alkyne coupling:  synthesis of the proposed structure of amphidinolide A. J Am Chem Soc. 2002;124:12420–12421.
   PubMedGoogle Scholar
• Imanzadeh GH, Aliabadi A, Zamanloo MR. Organic-salt-mediated highly regioselective N3-alkylation of 2-thiophenytoin via Michael reaction under solvent-free conditions. Green Chem Lett Rev. 2016;9:106–113.
   Web of Science ®Google Scholar
• Imanzadeh GH, Rezaee-Gatar S. Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation. Arkivoc. 2015;v:121–133.
   Google Scholar
• Bonabi S, Imanzadeh GH, Asgharzadeh R, et al. K2CO3/TBAB, a composite of inorganic and organic salts, a novel and powerful media for regioselective Michael addition of dihydropyrimidinones to acrylic esters under and without solvent conditions. Lett Org Chem. 2022;19:1118–1127.
   Web of Science ®Google Scholar
• Maram L, Tanaka F. Switching electrophile intermediates to nucleophiles: Michael and oxa-diels–alder reactions to afford polyoxy-functionalized piperidine derivatives with tetrasubstituted carbon. Org Lett. 2020;22:2751–2755.
   PubMed Web of Science ®Google Scholar
• Hrabalek A, Pus L, Baranek V, et al. Synthesis of unsymmetrical sulfides derived from tetrazole-5-thiols. Chem Heterocycl Compounds. 2002;38:183–189.
   Google Scholar
• Duffy BC, Howard KT, Chisholm JD. Alkylation of thiols with trichloroacetimidates under neutral conditions. Tetrahedron Lett. 2014;56:3301–3305.
   Web of Science ®Google Scholar
• Li LL, Gao LX, Han FS. A straightforward synthesis of alkyl 1H-tetrazol-5-yl thioethers via a one-pot reaction of aldehydes and 1H-tetrazole-5-thiols mediated by N-tosylhydrazones. RSC Adv. 2015;5:29996–30000.
   Web of Science ®Google Scholar