Regioselective synthesis of new 2,5,6-trisubstituted 5,6-dihydro-2H-pyrazolo[3,4-d]thiazoles from 5-dimethylaminoethylene-thaozolidin-4-thiones

References

• Chang-Ji Z, Li-Li X, Liang-Peng S, Jing M, Hu-Ri P. Synthesis and antibacterial activity of novel 1,3-diphenyl-1H-pyrazoles functionalized with phenylalanine-derived rhodanines. Eur J Med Chem. 2012;58:112–116. doi: 10.1016/j.ejmech.2012.10.012
   PubMed Web of Science ®Google Scholar
• Furlan A, Colombo F, Kover A, Issaly N, Tintori C, Angeli L, Leroux V, Letard S, Amat, M, Asses Y, Maigret B, Dubreuil P, Botta M, Dono R, Bosch J, Piccolo O, Passarella D, Maina F. Identification of new amino acid amides containing the imidazo[2,1-b]benzothiazol 2-ylphenyl moiety as inhibitors of tumorigenesis by oncogenic Met signalling. Eur J Med Chem. 2012;47:239–254. doi: 10.1016/j.ejmech.2011.10.051
   PubMed Web of Science ®Google Scholar
• Samet M, Kasmogullar R, Tuba I, Ferdag C, Ahmet A, Salim O. Synthesis, structure-activity relationships, and in vitro antibacterial and antifungal activity evaluations of novel pyrazole carboxylic and dicarboxylic acid derivatives. Eur J Med Chem. 2014;78:86–96. doi: 10.1016/j.ejmech.2014.03.033
   PubMed Web of Science ®Google Scholar
• Winters G, Sala A, Barone D, Baldoli E. Synthesis, in vitro [3H]prazosin displacement, and in vivo activity of 3-aryl-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridines, a new class of antihypertensive agents. J Med Chem. 1985;28:934–940. doi: 10.1021/jm00145a015
   PubMed Web of Science ®Google Scholar
• Krapcho J, Turk CF. Bicyclic pyrazolines, potential central nervous system depressants and antiinflammatory agents. J Med Chem. 1979;22:207–210. doi: 10.1021/jm00188a018
   PubMed Web of Science ®Google Scholar
• Aymn ER, Mohamed IH, Randa EAM, Jehan AM, Farouk ME, Abdel-Megeid RE. Synthesis and antiviral evaluation of some new pyrazole and fused pyrazolopyrimidine derivatives. Bioorg Med Chem. 2008;16:7102–7106. doi: 10.1016/j.bmc.2008.06.054
   PubMed Web of Science ®Google Scholar
• Anderson JD, Cottam HB, Larson SB, Nord LD, Revankar GR, Robins RK. Synthesis of certain pyrazolo [3,4-d] pyrimidin-3-one nucleosides. Heterocycl Chem. 1990;27:439–453. doi: 10.1002/jhet.5570270262
   Web of Science ®Google Scholar
• Al-Adiwish WM, Tahir MIM, Siti-Noor-Adnalizawati A, Hashim SF, Ibrahim N, Yaacob WA. Synthesis, antibacterial activity and cytotoxicity of new fused pyrazolo[1,5-a]pyrimidine and pyrazolo[5,1-c][1,2,4]triazine derivatives from new 5-aminopyrazoles. Eur J Med Chem. 2013;64:464–476. doi: 10.1016/j.ejmech.2013.04.029
   PubMed Web of Science ®Google Scholar
• Takahashi H, Shinoyama M, Komine T, Nagao M, Suzuki M, Tsuchida H, Katsuyama K. Novel dihydrothieno[2,3-e]indazole derivatives as IkB kinase inhibitors. Bioorg Med Chem Lett. 2011;21:1758–1762. doi: 10.1016/j.bmcl.2011.01.069
   PubMed Web of Science ®Google Scholar
• Vicentini CB, Veronese AC, Guarneri M, Manfrini M, Giori, P. A new synthesis of pyrazolo[3,4-d]thiazoles. Heterocycles. 1993;36:857–863. doi: 10.3987/COM-92-6254
   Google Scholar
• Chande MS, Carvalho PVR. Spiro-bithiazole derivatives of amidinothiocarbamides: novel utilization of the synthon 2- arylimino-5-carbethoxy-thiazolidin-4-one. Indian J Chem. 2004;43B:378–384.
   Google Scholar
• L'abbe G, D'hooge B, Dehaen W. Unusual behaviour of 4,5-dichloro-1,2,3-dithiazolium chloride (Apple's salt) with 5-aminopyrazoles: a synthetic method of 1H-pyrazolo[3,4-d]thiazoles. J Chem Soc Perkin Trans. 1995;1:2379–2380. doi: 10.1039/p19950002379
   Google Scholar
• Mohareb RM, Zohdi HF, Wardakhan WW. Reaction of 3-phenyl-5-aminopyrazole with carbon disulfide: a novel synthesis of 3-(3’-phenylpyrazol-5’-yl)-4-phenylpyrazol-2-thione as well as of pyrazolo[3,4-d]thiazole and pyrano[2,3-d]thiazole derivatives. Monatsh Chem. 1995;126:1391–1400. doi: 10.1007/BF00807069
   Google Scholar
• Waganat WW, Fleita DH, Mohareb RM. Reaction of 4-aryl-3-thiosemicarbazides with phenylisothiocyanate: a facile synthesis of thiazole, pyrazole and pyrimidine derivatives. J Chin Chem Soc. 1999;46:97–104.
   Web of Science ®Google Scholar
• Gautam D, Gautam P, Chaudhary RP. N-methylpyridinium tosylate catalysed green and efficient synthesis of some novel 2,4-disubstituted thiazoles and 4-thiazolidinones. Chin Chem Lett. 2012;23:1221–1224. doi: 10.1016/j.cclet.2012.10.002
   Web of Science ®Google Scholar
• Gautam P, Chaudhary RP. Carbodiimide mediated synthesis of new thiazolidin-4-ones and thiazinan-4-ones from thiosemicarbazone derivatives of 6,7-dihydro-1H-indazole-4(5H)-ones. J Chem Res. 2014;38:226–230. doi: 10.3184/174751914X13940194215183
   Web of Science ®Google Scholar
• Desai KG, Desai KR. A facile microwave enhanced of sulfur-containing five membered heterocycles derived from 2-mercaptobenzothiazole over synthesis ZnCl2/DMF and antimicrobial evaluation. J Sulfur Chem. 2006;27:315–328. doi: 10.1080/17415990600786409
   Web of Science ®Google Scholar
• Sharma RC, Kumar D. Synthesis of some new thiazolidin-4-ones as possible antimicrobial agents. J Indian Chem Soc. 2000;77:492–493.
   Web of Science ®Google Scholar
• Srivastava T, Haq, W, Katti SB. Carbodiimide mediated synthesis of 4-thiazolidinones by one-pot, three-component condensation. Tetrahedron. 2002;58:7619–7624. doi: 10.1016/S0040-4020(02)00866-9
   Web of Science ®Google Scholar
• Li X, Qin T, Yang T. Synthesis and biological activities of bi/tricyclic azasugars fused thiazolidin-4-one and thiazinan-4-one by microwave-assisted tandem Staudinger/aza-Wittig/cyclization. Bioorg Med Chem Lett. 2012;22:2712–2716. doi: 10.1016/j.bmcl.2012.02.103
   PubMed Web of Science ®Google Scholar
• Gouvea DP, Bareno VDO, Bosenbecker J, Drawanz BB, Neuenfeldt PD, Siqueira GM, Cunico W. Ultrasonics promoted synthesis of thiazolidinones from 2-aminopyridine and 2-picolilamine. Ultrason Sonochem. 2012;19:1127–1131. doi: 10.1016/j.ultsonch.2012.03.004
   PubMed Web of Science ®Google Scholar
• Lingampalle D, Jawale D, Waghmare R, Mane R. Ionic liquid-mediated, one-pot synthesis for 4-thiazolidinones. Synth Commun. 2010;40:2397–2401. doi: 10.1080/00397910903245174
   Web of Science ®Google Scholar
• Gautam D, Gautam P, Chaudhary RP. Expedient and green synthesis of some novel 4-thiazolidinones and new 2,4-disubstituted thiazoles with tetrahydro carbazole pendant. Lett Org Chem. 2012;9:660–663. doi: 10.2174/157017812803521081
   Google Scholar
• Rajanarendar E, Afzal M, Karunakar D. Synthesis of isoxazolylpyrazolo[3,4-d]thiazoles and isoxazolylthiazoles and their antibacterial and antifungal activity. Indian J Chem. 2004;43B:168–173.
   Google Scholar
• Zuhal T, Cigdem Y, Feray A, Emine B, Nuket O. Synthesis of new pyrazolothiazole derivatives from 4-thiazolidinones. Molecules. 2007;12(9):2151–2159. doi: 10.3390/12092151
   PubMed Web of Science ®Google Scholar
• Pelletier S, Pinson B, Smejkal T, Lamberth C. A general synthesis of tetrahydropyrazolo[3,4-d]thiazoles. Tetrahedron. 2013;69:4641–4651. doi: 10.1016/j.tet.2013.04.002
   Web of Science ®Google Scholar
• Tumul S, Anil KG, Wahajul H, Sudhir S, Setu BK. Synthesis and biological evaluation of 4-thiazolidinone derivatives as potential antimycobacterial agents. ARKIVOC. 2005;(ii):120–130.
   Google Scholar
• Becke AD. Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38:3098–3100. doi: 10.1103/PhysRevA.38.3098
   PubMed Web of Science ®Google Scholar
• Sheldrick GM. SHELXTL-97, program for refinement of crystal structure. Göttingen: University of Göttingen; 1997.
   Google Scholar