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Invited Article

A review of self-organising 2,5- and 2,4-disubstituted 1,3-thiazole-containing materials: synthesis, mechanisms and tactics

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Pages 1894-1910 | Received 11 May 2017, Published online: 06 Jul 2017

References

  • Goodby JW, Mandle RJ, Davis EJ, et al. What makes a liquid crystal? The effect of free volume on soft matter. Liq Cryst. 2015;42:593–622.
  • Al-Awadi N, Taylor R. The mechanism of thermal eliminations. Part 21. Rate data for pyrolysis of 2-ethoxyquinoline, 1- and 3-ethoxyisoquinoline, and 1-ethoxythiazole: correlation of reactivities with π-bond order of the C=N bond. J Chem Soc Perkin Trans 2. 1986;1589–1592.
  • Clark RF, Zhang T, Wang X, et al. Phenoxy thiazole derivatives as potent and selective acetyl-CoA carboxylase 2 inhibitors: modulation of isozyme selectivity by incorporation of phenyl ring substituents. Bioorg Med Chem Lett. 2007;17:1961–1965.
  • Barlow JJ, Block MH, Hudson JA, et al. Acid-catalyzed racemization of 1-(heterocyclyloxy)-2,3-propanediols. J Org Chem. 1992;57:5158–5162.
  • Burger K, Ottlinger R, Goth H, et al. Reaction behavior of trifluoromethyl groups synthesis of 1,3-azoles from trifluoromethyl-substituted hetero-1,3-dienes. Chem Ber. 1982;115:2494–2507.
  • Gillies I, Rees CW. Amide anions as unexpected activating groups in nucleophilic heteroaromatic substitution. Tetrahedron Lett. 1996;37:4065–4068.
  • Kvitko IY, Smirnova VA, El’tsov AV. Research on aminomethylene derivatives of azole. 24. Cyclization of thiohippuric acid in the presence of the vilsmeier reagent. Chem Heterocycl Comp. 1980;16:28–31. Translated from: Khimiya Geterotsiklicheskikh Soedinenii, 1997, (11), pp 1559-1560.
  • Ottlinger R, Burger K, Goth H, et al. A new strategy for the synthesis of partially fluorinated 1,3-azoles. Tetrahedron Lett. 1978;5003–5006.
  • Bosco M, Forlani L, Todesco PE, et al. Relative reactivity of groups bonded to positions 2 and 5 of the thiazole ring. J Chem Soc Perkin Trans 2. 1976;398–402.
  • Van Zyl G, Langenberg RJ, Tan HH, et al. Condensations of aldehydes with 2-thienyllithium, 2-thienylsodium and 2-thienylmagnesium bromide. J Am Chem Soc. 1956;78:1955–1958.
  • Bordwell FG. Equilibrium acidities in dimethyl sulfoxide solution. Acc Chem Res. 1988;21:456–463.
  • Dondoni A, Merino P. Thiazoles. In: Katrizky AR, Rees CW, Scriven EFV, editors. Comprehensive heterocyclic chemistry II the structure, reactions, synthesis and uses of heterocyclic compounds five-membered rings with two heteroatoms and fused carbocyclic derivatives. Comprehensive heterocyclic chemistry. 3 ed. Oxford: Elsevier science Ltd; 1996. p. 373–474.
  • Ganapathi K, Venkataraman A. Chemistry of the thiazoles. I. Synthesis of 5-amino-thiazole derivatives. Proc Indian Acad Sci, Section A. 1945;22A:343–358.
  • Ganapathi K, Kulkarni KD. Chemistry of the thiazoles. V. Fine structure and orientation. Proc Indian Acad Sci, Section A. 1953;38A:45–57.
  • Takami S, Irie M. Synthesis and photochromic properties of novel yellow developing photochromic compounds. Tetrahedron. 2004;60:6155–6161.
  • Jacobi PA, Egbertson M, Frechette RF, et al. Thiazoles in organic-synthesis. Novel syntheses of menthanes and eremophilanes. Tetrahedron. 1988;44:3327–3338.
  • Poite M, Metzger J. New syntheses in the 5-alkyl-and 2,5-dialkylthiazole series. Bull Soc Chim Fr. 1962;2078–2085.
  • Steliou K, Mrani M. Tin-assisted sulfuration: a highly potent new method for the conversion of carbonyl units into their corresponding thiocarbonyl analogs. J Am Chem Soc. 1982;104:3104–3106.
  • Freeman F, Kim DHSL, Rodriguez E. Preparation of 1,4-diketones and their reactions with bis(trialkyltin) or bis(triphenyltin) sulfide-boron trichloride. J Org Chem. 1992;57:1722–1727.
  • Thomsen I, Pedersen U, Rasmussen PB, et al. Novel and convenient methods for the preparation of substituted thiophenes, thiazoles, and 1,3,4-thiadiazole-2(3H)-thiones from bifunctional substrates. Chem Lett. 1983;12:809–810.
  • Cava MP, Levinson MI. Thionation reactions of Lawesson’s reagents. Tetrahedron. 1985;41:5061–5087.
  • Jesberger M, Davis TP, Barner L. Applications of Lawesson’s reagent in organic and organometallic syntheses. Synthesis. 2003;1929–1958.
  • Ozturk T, Ertas E, Mert O. Use of Lawesson’s reagent in organic syntheses. Chem Rev. 2007;107:5210–5278.
  • Babadjamian A, Gallo R, Metzger J, et al. Study of the mechanism of the Hantzsch thiazole reaction. II. Primary step: reaction of the α-halo ketones with thio amides. J Heterocycl Chem. 1976;13:1205–1208.
  • Grubb AM, Hasan S, Kiryanov AA, et al. The synthesis and physical evaluation of 5-alkoxy-1,3-thiazoles prepared via Lawesson’s reagent-mediated cyclisation of α-benzamido esters. Liq Cryst. 2009;36:443–453.
  • Grubb AM, Zhang C, Jákli A, et al. 2-Alkoxy-1,3-thiazoles: a new core unit for incorporation into self-organizing materials. Synthetic approach, mesomorphism, and electrooptic evaluation. Liq Cryst. 2012;39:1175–1195.
  • Kiryanov AA, Sampson P, Seed AJ. Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson’s reagent-mediated cyclization under microwave irradiation: applications for liquid crystal synthesis. J Org Chem. 2001;66:7925–7929.
  • Penney CL, Shah P, Landi S. A simple method for the synthesis of long-chain alkyl esters of amino acids. J Org Chem. 1985;50:1457–1459.
  • Zheng M-H, Jin J-Y, Sun W, et al. A new series of fluorescent 5-methoxy-2-pyridylthiazoles with a pH-sensitive dual-emission. New J Chem. 2006;30:1192–1196.
  • Grubb AM. Preparation of heteroatom-substituted 1,3-thiazoles as building blocks for liquid crystal synthesis [Ph.D. Thesis]: Kent State University; December 2011.
  • Kaleta Z, Makowski BT, Soós T, et al. Thionation using fluorous Lawesson’s reagent. Org Lett. 2006;8:1625–1628.
  • Kaleta Z, Tárkányi G, Gömöry A, et al. Synthesis and application of a fluorous Lawesson’s reagent: convenient chromatography-free product purification. Org Lett. 2006;8:1093–1095.
  • Legnani L, Toma L, Caramella P, et al. Computational mechanistic study of thionation of carbonyl compounds with Lawesson’s reagent. J Org Chem. 2016;81:7733–7740.
  • Höfle G, Steglich W, Vorbrüggen H. New synthetic methods 25. 4-Dialkylaminopyridines as highly active acylation catalysts. Angew Chem. Int Ed Engl. 1978;17:569–583.
  • Neises B, Steglich W. 4-dialkylaminopyridines as acylation catalysts. Part 5. Simple method for the esterification of carboxylic acids. Angew Chem Int Ed. 1978;17:522–524.
  • Hassner A, Alexanian V. Direct room temperature esterification of carboxylic acids. Tetrahedron Lett. 1978;19:4475–4478.
  • Tuzimoto P, Santos DMPO, Moreira TDS, et al. Luminescent liquid crystals containing a sulphur-based heterocyclic core. Liq Cryst. 2014;41:1097–1108.
  • Grubb AM, Schmidt MJ, Seed AJ, et al. Convenient preparation of halo-1,3-thiazoles: important building blocks for materials and pharmaceutical synthesis. Synthesis. 2012;44:1026–1029.
  • Strotman NA, Chobanian HR, He J, et al. Catalyst-controlled regioselective Suzuki couplings at both positions of dihaloimidazoles, dihalooxazoles, and dihalothiazoles. J Org Chem. 2010;75:1733–1739.
  • Bey E, Marchais-Oberwinkler S, Werth R, et al. Design, synthesis, biological evaluation and pharmacokinetics of bis(hydroxyphenyl) substituted azoles, thiophenes, benzenes, and aza-benzenes as potent and selective nonsteroidal inhibitors of 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1). J Med Chem. 2008;51:6725–6739.
  • Hird M, Toyne KJ. Fluoro substitution in thermotropic liquid crystals. Mol Cryst Liq Cryst. 1998;323:1–67.
  • Hird M, Goodby JW, Lewis RA, et al. The fascinating influence of fluoro substituents on the synthesis and properties of liquid crystals. Mol Cryst Liq Cryst. 2003;401:1–18.
  • Gray GW, Hird M, Toyne KJ. The synthesis and transition temperatures of some lateral monofluoro-substituted 4,4ʹ’-dialkyl- and 4,4ʹ’-alkoxyalkyl-1,1ʹ - 4ʹ,1ʹ’-terphenyls. Mol Cryst Liq Cryst. 1991;195:221–237.
  • Gray GW, Hird M, Lacey D, et al. The synthesis and transition temperatures of some 4,4”-dialkyl- and 4,4”-alkoxyalkyl-1,1ʹ:4ʹ,1”-terphenyls with 2,3- or 2ʹ,3ʹ-difluoro substituents and of their biphenyl analogues. J Chem Soc Perkin Trans II. 1989;2041–2053.
  • Kelly SM, Schad H. The synthesis and transition temperatures of ester derivatives of 2-fluoro-4-hydroxy and 3-fluoro-4-hydroxybenzonitriles also incorporating aliphatic ring systems. Helv Chim Acta. 1984;67:1580–1587.
  • Chambers M, Clemitson R, Coates D, et al. Laterally fluorinated phenyl biphenylcarboxylates; versatile components for ferroelectric smectic C mixtures. Liq Cryst. 1989;5:153–158.
  • Gray GW, Kelly SM. The liquid crystal properties of 4-n-alkyl and 4-n-alkoxy-phenyl 4-n-alkylbicyclo[2.2.2]octane-1-carboxylates. Mol Cryst Liq Cryst. 1981;75:95–108.
  • Pace A, Buscemi S, Vivona N. The synthesis of fluorinated heteroaromatic compounds. Part 2. Five-membered rings with two heteroatoms. A review. Org Prep Proced Int. 2007;39:1–70.
  • Grubb AM, Sampson P, Seed AJ. Manuscript in preparation. In preparation for submission to. Liq Cryst.
  • Beyerman HC, Berben PH, Bontekoe JS. The synthesis of thiazole-2- and of thiazole-5-carboxylic acid via a halogen-metal exchange reaction. Rec Trav Chim. 1954;73:325–332.
  • Nassif LA. New heterocyclic sulfur-containing liquid crystals for fast, defect-free ferroelectric display applications [M.S. Thesis]. Kent: Kent State University; 2000.
  • Carney SM, Koval T, Sampson P, et al. Unpublished work. 2016.
  • Erne M. The decarboxylation of carboxylic acids of thiazoles. Helv Chim Acta. 1953;36:138–141.
  • Ori M, Nishio T. Sulfur-containing heterocycles: facile synthesis of 4H-1,3-thiazines by the reaction of 3-N-acylamino ketones with Lawesson’s reagent. Heterocycles. 2000;52:111–116.
  • Kadam KS, Jadhav RD, Kandre S, et al. Evaluation of thiazole containing biaryl analogs as diacylglycerol acyltransferase 1 (DGAT1) inhibitors. Eur J Med Chem. 2013;65:337–347.
  • Pfefferkorn JA, Greene ML, Nugent RA, et al. Inhibitors of HCV NS5B polymerase. Part 1: evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid. Bioorg Med Chem Lett. 2005;15:2481–2486.
  • Ackrell J, Muchowski JM, Galeazzi E, et al. Alkylation of α-formamido ketone enolate anions. A versatile synthesis of α-alkyl α-amino ketones. J Org Chem. 1986;51:3374–3376.
  • Togo H, Fujii M, Yokoyama M. Conversion of hydroxyl groups in alcohols to other functional groups with N-hydroxy-2-thiopyridone, and its application to dialkylamines and thiols. Bull Chem Soc Jpn. 1991;64:57–67.
  • Tanaka C, Nasu K, Yamamoto N, et al. Pyrolysis of benzyl 2-oxazolecarbamates and benzyl 4- alkylallophanates. Chem Pharm Bull. 1982;30:4195–4198.
  • Schneider JMFM, Sales ES, Livotto PR, et al. Synthesis of new family of thiazoline and thiazole esters and investigation of their thermal properties. J Braz Chem Soc. 2014;25:1493–1503.
  • Zamri A, Abdallah MA. An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia. Tetrahedron. 2000;56:249–256.
  • Loughlin WA, Knevitt SA, Hosking RE, et al. Approaches to the high-throughput synthesis of analogues of dihydroaeruginoic acid. Aust J Chem. 2000;53:457–462.
  • Buckle DR. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone. Encyclopedia of reagents for organic synthesis. Chichester: John Wiley & Sons, Ltd; 2001.
  • Evans DL, Minster DK, Jordis U, et al. Nickel peroxide dehydrogenation of oxygen-, sulfur-, and nitrogen-containing heterocycles. J Org Chem. 1979;44:497–501.
  • Nakagawa K, Konaka R, Nakata T. Oxidation with nickel peroxide. I. Oxidation of alcohols. J Org Chem. 1962;27:1597–1601.
  • Phillips AJ, Uto Y, Wipf P, et al. Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor. Org Lett. 2000;2:1165–1168.
  • Murza MM, Prosochina TR, Safarov MG, et al. Synthesis and quantum-chemical study of liquid-crystal derivatives of thiazole. Chem Heterocycl Compd (New York NY, US). 2001;37:1258–1265.
  • Murza MM, Safarov MG. Mesomorphic thiazole derivatives. Russ J Org Chem. 2000;36:1201–1203.
  • Murza MM, Kuvatov ZK, Safarov MG. Geometry and mesomorphic properties of new Schiff bases containing thiazole ring. Chem Heterocycl Compd (New York NY, US). 1999;35:1097–1103.
  • Golovanov AS, Murza MM, Safarov MG. Novel mesomorphic Schiff bases. Chem Heterocycl Compd (New York, NY, US). 1997;33:1350–1351.
  • Murza MM, Golovanov AS, Safarov MG. Synthesis and investigation of mesomorphous properties of some thiazole derivatives. Russ J Org Chem. 1995;31:1529–1532.
  • Murza MM, Golovanov AS, Safarov MG. New liquid crystal derivatives of thiazole. Chem Heterocycl Compd (New York NY, US). 1996;32:477–478.
  • Kuvatov ZK, Safarov MG, Murza MM. New derivatives of thiazole with mesomorphous properties. Chem Heterocycl Compd (New York NY, US). 2004;40:500–502.
  • Golovanov AS, Dvoenko OV, Murza MM, et al. Mesomorphism of thiazole derivatives. Bashk Khim Zh. 1997;4:70–72.
  • Thaker BT, Patel P, Vansadia AD, et al. Synthesis, characterization, and mesomorphic properties of new liquid-crystalline compounds involving ester-azomethine central linkages, lateral substitution, and a thiazole ring. Mol Cryst Liq Cryst. 2007;466:13–22.
  • Dölling K, Zaschke H, Schubert H. Liquid crystal thiazoles. J Prakt Chem. 1979;321:643–654.
  • Lehmann M, Seltmann J, Auer AA, et al. Synthesis and mesomorphic properties of new V-shaped shape-persistent nematogens containing a thiazole or a thiadiazole bending unit. J Mater Chem. 2009;19:1978–1988.
  • Lehmann M, Seltmann J. Low temperature enantiotropic nematic phases from V-shaped, shape-persistent molecules. Beilstein J Org Chem. 2009;5. [ article number 73].
  • Mori A, Sekiguchi A, Masui K, et al. Facile synthesis of 2,5-diarylthiazoles via palladium-catalyzed tandem C-H substitutions. Design of tunable light emission and liquid crystalline characteristics. J Am Chem Soc. 2003;125:1700–1701.
  • Pivsa-Art S, Satoh T, Kawamura Y, et al. Palladium-catalyzed arylation of azole compounds with aryl halides in the presence of alkali metal carbonates and the use of copper iodide in the reaction. Bull Chem Soc Jpn. 1998;71:467–473.
  • Shikuma J, Mori A, Masui K, et al. Photoluminescent and liquid-crystalline properties of donor-acceptor-type 2,5-diarylthiazoles. Chem Asian J. 2007;2:301–305.
  • Mori A, Sugie A. Palladium-catalyzed CH arylation and dehydrogenative homocoupling of heteroaromatic compounds and application to the design of advanced organic materials. Bull Chem Soc Jpn. 2008;81:548–561.
  • Lee C-H, Yamamoto T. Synthesis of liquid crystals with bent-rod structure: 4-methylthiazole derivatives with nematic phase. Mol Cryst Liq Cryst. 2001;369:95–102.
  • Lee C-H, Yamamoto T. Synthesis of liquid crystals with bent-rod structure: mesogenic thiazole derivatives with long alkoxyl chains. Mol Cryst Liq Cryst. 2001;363:77–84.
  • Kitamura T, Lee CH, Taniguchi Y, et al. A new route to chiral diaryldiacetylenic liquid crystals. Preparation of iodonium salts bearing chiral alkynyl ligands and utility for chiral alkynyl transfer agents. J Am Chem Soc. 1997;119:619–620.
  • Liu X, Huang Y, Cao Z, et al. Synthesis and photovoltaic properties of copolymers based on benzo[1,2-b:4,5-b’]dithiophene and thiazole with different conjugated side groups. Polym Chem. 2013;4:4737–4745.
  • Arora A, Teegardin KA, Weaver JD. Reductive alkylation of 2-bromoazoles via photoinduced electron transfer: a versatile strategy to Csp2-Csp3 coupled products. Org Lett. 2015;17:3722–3725.

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