3,4-Dimethyl-2,5-functionalized thieno[2,3-b]thiophenes: versatile precursors for novel bis-thiazoles

References

• Mabkhot YN. Synthesis and chemical characterisation of new bis-thieno[2,3-b]thiophene derivatives. Molecules. 2010;15:3329–3337. doi: 10.3390/molecules15053329
   PubMed Web of Science ®Google Scholar
• Mabkhot YN, Kheder NA, Al-Majid AM. Facile and convenient synthesis of new thieno[2,3-b]thiophene derivatives. Molecules. 2010;15:9418–9426. doi: 10.3390/molecules15129418
   PubMed Web of Science ®Google Scholar
• Mabkhot YN. Synthesis and analysis of some bis-heterocyclic compounds containing sulphur. Molecules. 2009;14:1904–1914. doi: 10.3390/molecules14051904
   PubMed Web of Science ®Google Scholar
• Mabkhot YN, Assem Barakat AM, Al-Majid Alshahrani SA. Comprehensive and facile synthesis of some functionalized bis-heterocyclic compounds containing a thieno[2,3-b]thiophene motif. Int J Mol Sci. 2012;13:2263–2275. doi: 10.3390/ijms13022263
   PubMed Web of Science ®Google Scholar
• Jarak I, Kralj M, Piantanida I, Suman L, Zinic M, Pavelic K, Karminski-Zamola G. Novel cyano- and amidino-substituted derivatives of thieno[2,3-b]- and thieno[3,2-b]thiophene-2-carboxanilides and thieno[3′,2′:4,5]thieno- and thieno[2′,3′:4,5]thieno [2,3-c]quinolones: synthesis, photochemical synthesis, DNA binding, and antitumor evaluation. Bioorg Med Chem. 2006;14:2859–2868. doi: 10.1016/j.bmc.2005.12.004
   PubMed Web of Science ®Google Scholar
• Garnier F. Functionalized conducting polymers-towards intelligent materials. Angew Chem. 1989;101:529–533; Angew Chem Int Ed Engl. 1989; 28: 513–517. doi: 10.1002/ange.19891010447
   Google Scholar
• Bedworth PV, Cai Y, Jen A, Marden SR. Synthesis and relative thermal stabilities of diphenylamino- vs piperidinyl-substituted bithiophene chromophores for nonlinear optical materials. J Org Chem. 1996;61:2242–2246. doi: 10.1021/jo9517555
   Web of Science ®Google Scholar
• Burland DM, Miller RD, Walsh CA. Second-order nonlinearity in poled-polymer systems. Chem Rev. 1994;94:31–75. doi: 10.1021/cr00025a002
   Web of Science ®Google Scholar
• Takahashi K, Ogiyama M. 2,5-Bis(3,5-di-t-butyl-4-oxo-cyclohexa-2,5-dien-1-ylidene)-2,5-dihydro-1,4-dithiapentalene: a new class of amphoteric multistage redox systems consisting of both the Wurster and the Weitz types. J Chem Soc Chem Commun. 1990;1196–1198.
   Google Scholar
• Litvinov VP. The latest achievements in thienothiophene chemistry. Russ Chem Rev. 2005;74:217–248. doi: 10.1070/RC2005v074n03ABEH000889
   Google Scholar
• Gather MC, Heeny M, Zhang W, Whitehead KS, Bradley DDC, McCulloch I, Campbell A. An alignable fluorene thienothiophene copolymer with deep-blue electroluminescent emission at 410 nm. Chem Commun. 2008;1079–1081. doi: 10.1039/b716510b
   PubMed Web of Science ®Google Scholar
• He M, Li J, Sorensen ML, Zhang F, Hancock RR, Fong HH, Pozdin VA, Smilgies D, Malliaras GG. Alkylsubstituted thienothiophene semiconducting materials: structure-property relationships. J Am Chem Soc. 2009;131:11930–11938. doi: 10.1021/ja903895s
   PubMed Web of Science ®Google Scholar
• Mahler G, Serra G, Dematteis S, Saldaňa J, Domínguez L, Manta E. Synthesis and biological evaluation of simplified mycothiazole analogues. Bioorg Med Chem Lett. 2006;16:1309–1311. doi: 10.1016/j.bmcl.2005.11.072
   PubMed Web of Science ®Google Scholar
• Tapia RA, Alegria L, Pessoa CD, Salas C, Cortés MJ, Valderrama JA, Sarciron ME, Pautet F, Walchshofer N, Fillion H. Synthesis and antiprotozoal activity of napthfuranquinones and napthothiophenequinones containing a fused thiazole ring. Bioorg Med Chem. 2003;11:2175–2182. doi: 10.1016/S0968-0896(03)00122-6
   PubMed Web of Science ®Google Scholar
• Bonde CG, Gaikwad NJ. Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial agents. Bioorg Med Chem. 2004;12:2151–2161. doi: 10.1016/j.bmc.2004.02.024
   PubMed Web of Science ®Google Scholar
• Pontillo J, Chen C. Efficient synthesis of bicyclic oxazolino- and thiazolino[3,2-c]pyrimidine-5,7-diones and its application to the synthesis of GnRH antagonists. Bioorg Med Chem Lett. 2005;15:1407–1411. doi: 10.1016/j.bmcl.2005.01.009
   PubMed Web of Science ®Google Scholar
• Pontiki E, Hadjipavlou LD, Chaviara AT, Bolos CA. Comparison of the antiplasmodial and falcipain-2 inhibitory activity of β-amino alcohol thiolactone-chalcone and isatin-chalcone hybrids. Bioorg Med Chem Lett. 2006;16:2234–2237. doi: 10.1016/j.bmcl.2006.01.045
   PubMed Web of Science ®Google Scholar
• Barros GF, Bernalte GA, Higes RFJ, Luna GF, Maldonado RMA, Vinuelas ZE. Synthesis, crystal structure, spectroscopic and magnetic properties of copper(II) complexes with 2-(2-pyridyl)imino-N-(2-thiazolin-2-yl)thiazolidine (PyTT). Inorg Chim Acta. 2004;357:3574–3582. doi: 10.1016/j.ica.2004.04.001
   Web of Science ®Google Scholar
• Küçükgüzel G, Kocatepe A, Clercq ED, Şahin F, Güllüce M. Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide. Eur J Med Chem. 2006;41:353–359. doi: 10.1016/j.ejmech.2005.11.005
   PubMed Web of Science ®Google Scholar
• Verma A, Saraf SK. 4-Thiazolidinone: a biologically active scaffold. Eur J Med Chem. 2008;43:897–905. doi: 10.1016/j.ejmech.2007.07.017
   PubMed Web of Science ®Google Scholar
• Abdel-Wahab BF, Mohamed SF, Amr AEl-GE, Abdalla MM. Synthesis and reactions of thiosemicarbazides, triazoles, and Schiff bases as antihypertensive α-blocking agents. Monatsh Chem. 2008;139:1083–1090. doi: 10.1007/s00706-008-0896-2
   Web of Science ®Google Scholar
• Thurston DE, Bose DS, Thompson AS, Howard PW, Leoni A, Croker SJ, Jenkins TC, Neidle S, Hartley JA, Hurley LH. Synthesis of sequence-selective C8-linked pyrrolo[2,1-c][1,4]benzodiazepine DNA interstrand cross-linking agents. J Org Chem. 1996;61:8141–8147. doi: 10.1021/jo951631s
   PubMed Web of Science ®Google Scholar
• Shaker RM. One-pot synthesis of novel 1,1′- and 1,4-bridged bis-thiazolidinone derivatives and their antimicrobial activity. Phosphorus Sulfur Silicon Relat Elem. 1999;149:7–14. doi: 10.1080/10426509908037017
   Web of Science ®Google Scholar
• Kamal A, Laxman N, Ramesh G, Neelima K, Anand KK. Synthesis of novel non-cross-linking pyrrolobenzodiazepines with remarkable DNA binding affinity and potent antitumour activity. Chem Commun. 2001;437–438.
   Google Scholar
• Raasch A, Scharfenstein O, Trankle C, Holzgrabe U, Mohr K. Elevation of ligand binding to muscarinic M2 acetylcholine receptors by bis(ammonio)alkane-type allosteric modulators. J Med Chem. 2002;45:3809–3812. doi: 10.1021/jm020871e
   PubMed Web of Science ®Google Scholar
• Jain M, Khanna P, Saxena A, Bhagat S, Olsen CE, Jain SC. Synthesis of some novel bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4'-diones. Synth Commun. 2006;36:1863–1872. doi: 10.1080/00397910600602560
   Web of Science ®Google Scholar
• Jain M, Sakhuja R, Khanna P, Bhagat S, Jain SC. A facile synthesis of novel unsymmetrical bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4'-diones. Arkivoc. 2008;xv:54–64. doi: 10.3998/ark.5550190.0009.f07
   Google Scholar
• Yang GY, Oh K-A, Park N-J, Jung Y-S. New oxime reactivators connected with CH2O(CH2)nOCH2 linker and their reactivation potency for organophosphorus agents-inhibited acetylcholinesterase. Bioorg Med Chem. 2007;15:7704–7710. doi: 10.1016/j.bmc.2007.08.056
   PubMed Web of Science ®Google Scholar
• Giacomo BD, Bedini A, Spadoni G, Tarzia G, Fraschini F, Pannaccib M, Lucinib V. Synthesis and biological activity of new melatonin dimeric derivatives. Bioorg Med Chem. 2007;15:4643–4650. doi: 10.1016/j.bmc.2007.03.080
   PubMed Web of Science ®Google Scholar
• Holla BS, Gonsalves R, Shenoy S. Synthesis and antibacterial studies of a new series of 1,2-bis(1,3,4-oxadiazol-2-yl)ethanes and 1,2-bis(4-amino-1,2,4-triazol-3-yl)ethanes. Eur J Med Chem. 2000;35:267–271. doi: 10.1016/S0223-5234(00)00154-9
   PubMed Web of Science ®Google Scholar
• Holla BS, Gonsalves R, Rao BS, Shenoy S, Gopalakrishna HN. Synthesis of some new biologically active bis-(thiadiazolotriazines) and bis-(thiadiazolotriazinyl) alkanes. Il Farmaco. 2001;56:899–903. doi: 10.1016/S0014-827X(01)01119-3
   PubMedGoogle Scholar
• Holla BS, Poojary KN, Rao BS, Shivananda MK. New bis-aminomercaptotriazoles and bis-triazolothiadiazoles as possible anticancer agents. Eur J Med Chem. 2002;37:511–517. doi: 10.1016/S0223-5234(02)01358-2
   PubMed Web of Science ®Google Scholar
• Li JT, Sun MX, He GY, Xu XY. Efficient and green synthesis of bis(indolyl)methanes catalyzed by ABS in aqueous media under ultrasound irradiation. Ultrason Sonochem. 2011;18:412–414. doi: 10.1016/j.ultsonch.2010.07.016
   PubMed Web of Science ®Google Scholar
• Wang Z, Zhao C, Zhao D, Li C, Ahang J, Wang H. The preparation of substituted bithiophenyl aldehydes via the ring opening of dithieno[2,3-b:3′,2′-d]thiophene in the presence of n-BuLi. Tetrahedron. 2010;66:2168–2174. doi: 10.1016/j.tet.2010.01.056
   Web of Science ®Google Scholar
• Diana P, Carbone A, Barraja P, Kelter G, Fiebig H, Cirrincione G. Synthesis and antitumor activity of 2,5-bis(3′-indolyl)-furans and 3,5-bis(3′-indolyl)-isoxazoles, nortopsentin analogues. Bioorg Med Chem. 2010;18:4524–4529. doi: 10.1016/j.bmc.2010.04.061
   PubMed Web of Science ®Google Scholar
• Toyota K, Okada K, Katsuta H, Morita N. Chemistry of Bis(2-ethynyl-3-thienyl)arene and related systems. Part 2: "preparations of bis[2-(2-arylethynyl)-3-thienyl]arenes and bis[2-{2-(trimethylsilyl)ethynyl}-3-thienyl]arenes. Tetrahedron. 2009;65:145–151. doi: 10.1016/j.tet.2008.10.088
   Web of Science ®Google Scholar
• Todd EM, Zimmerman SC. Bis-ureidodeazapterin (Bis-DeAP) as a general route to supramolecular star polymers. Tetrahedron. 2008;64:8558–8570. doi: 10.1016/j.tet.2008.05.076
   Web of Science ®Google Scholar
• Diana P, Carbone A, Barraja P, Montalbano A, Martorana A, Dattolo G, Gia O, Dalla Via L, Cirrincione G. Synthesis and antitumor properties of 2,5-bis(3′-indolyl)thiophenes: analogues of marine alkaloid nortopsentin. Bioorg Med Chem Lett. 2007;17:2342–2346. doi: 10.1016/j.bmcl.2007.01.065
   PubMed Web of Science ®Google Scholar
• Blanco G, Quintela JM, Peinador C. Efficient one-pot preparation of bis(pyrazino[2′,3′:4,5]thieno[3,2-d]pyrimidin-4-yl)benzenes based on an aza-Wittig/mediated annulation strategy. Tetrahedron. 2007;63:2034–2041. doi: 10.1016/j.tet.2006.12.049
   Web of Science ®Google Scholar
• Promarak V, Punkvuang A, Jungsuttiwong S, Saengsuwan S, Sudyoadsuk T, Keawin T. Synthesis, optical, electrochemical, and thermal properties of α,α′-bis(9,9-bis-n-hexylfluorenyl) substituted oligothiophenes. Tetrahedron Lett. 2007;48:3661–3665. doi: 10.1016/j.tetlet.2007.03.131
   Web of Science ®Google Scholar
• Comel A, Kirsch G. Efficient one pot preparation of variously substituted thieno[2,3-b] thiophene. J Heterocyclic Chem. 2001;38:1167–1171. doi: 10.1002/jhet.5570380521
   Web of Science ®Google Scholar
• Mabkhot YN, Al-Majid AM, Alamary AS, Warad I, Sedigi Y. Reactions of some new thienothiophene derivatives. Molecules. 2011;16:5142–5148. doi: 10.3390/molecules16065142
   PubMed Web of Science ®Google Scholar
• Mashraqui SA, Sangvikar YS, Ghadigaonkar SG, Ashraf M, Meetsma M. Oxa-bridged cyclophanes featuring thieno[2,3-b]thiophene and C2-symmetric binol or bis-naphthol rings: synthesis, structures, and conformational studies. Tetrahedron. 2008;64:8837–8842. doi: 10.1016/j.tet.2008.06.076
   Web of Science ®Google Scholar
• Mekky AEM, Elwahy AHM. Synthesis of novel benzo-substituted macrocyclic ligands containing thienothiophene subunits. J Heterocyclic Chem. 2014;51:34–41. doi: 10.1002/jhet.2012
   Web of Science ®Google Scholar
• Sah PPT, Daniels TC. Thiosemicarbazide as a reagent for the identification of aldehydes, ketones, and quinones. Recl. Trav. Chim. Pays-Bas. 1950;69:1545–1556. doi: 10.1002/recl.19500691211
   Google Scholar
• Shih M-H, Su Y-S, WU C-L. Syntheses of aromatic substituted hydrazino-thiazole derivatives to clarify structural characterization and antioxidant activity between 3-arylsydnonyl and aryl substituted hydrazino-thiazoles. Chem Pharm Bull. 2007;55:1126–1135. doi: 10.1248/cpb.55.1126
   PubMed Web of Science ®Google Scholar