412
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Synthetic pathway for a new series of liquid crystal 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazole

, , , &
Pages 570-580 | Received 13 Jan 2013, Accepted 17 Feb 2013, Published online: 11 Mar 2013

References

  • Vlachos , P , Mansoor , B , Aldred , MP , O'Neill , M and Kelly , SM. 2005 . Charge-transport in crystalline organic semiconductors with liquid crystalline order . Chem Commun , : 2921 – 2923 .
  • Sonar , P , Singh , SP , Sudhakar , S , Dodabalapur , A and Sellinger , A. 2008 . High-mobility organic thin film transistors based on benzothiadiazole-sandwiched dihexylquaterthiophenes . Chem Mater , 20 : 3184 – 3190 .
  • Cristiano , R , Ely , F and Gallardo , H. 2005 . Light-emitting bent-shape liquid crystals. Liq . Crystal , 32 : 15 – 25 .
  • Hassheider , T , Benning , SA , Kitzerow , HS , Achard , MF and Bock , H. 2001 . Color-tuned electroluminescence from columnar liquid crystalline alkyl arenecarboxylates . Angew Chem Int Ed , 40 : 2060 – 2063 .
  • Ramón-Gimenez , L , Storz , R , Haberl , J , Finkelmann , H and Hoffmann , A. 2012 . Anisotropic ionic mobility of lithium salts in lamellar liquid crystalline polymer networks . Macromol Rapid Commun , 33 : 386 – 391 .
  • Kaafarani , BR. 2011 . Discotic liquid crystals for opto-electronic applications . Chem Mater , 23 : 378 – 396 .
  • Pisula , W , Zorn , M , Chang , JY , Müllen , K and Zentel , R. 2009 . Liquid crystalline ordering and charge transport in semiconducting materials . Macromol Rapid Commun , 30 : 1179 – 1202 .
  • Cristiano , R , Gallardo , H , Bortoluzzi , AJ , Bechtold , IH , Campos , CEM and Longo , RL. 2008 . Tristriazolotriazines: a core for luminescent discotic liquid crystals . Chem Commun , : 5134 – 5136 .
  • Cristiano , R , Eccher , J , Bechtold , IH , Tironi , CN , Vieira , AA , Molin , F and Gallardo , H. 2012 . Luminescent columnar liquid crystals based on tristriazolotriazine . Langmuir , 28 : 11590 – 11598 .
  • Pinto , AVA , Vencato , I , Gallardo , HA and Mascarenhas , YP. 1987 . X-ray crystal-structures and directional diamagnetic susceptibility calculations of decyl and dodecylammonium chlorides . Mol Cryst Liq Cryst , 149 : 29 – 40 .
  • Demus , D , Goodby , J , Gray , GW , Spiess , HW and Vill , V. 1998 . “ Handbook of liquid crystals ” . In Low molecular weight liquid crystals I , Weinheim : VCH-Wiley . Vol. 2A
  • Cristiano , R , Westphal , E , Bechtold , IH , Bortoluzzi , AJ and Gallardo , H. 2007 . Synthesis and optical/thermal properties of low molecular mass V-shaped materials based on 2,3-dicyanopyrazine . Tetrahedron , 63 : 2851 – 2858 .
  • Bartulín , J , Martinez , R , Gallardo , H , Muller , H and Taylor , TR. 1993 . Synthesis and mesomorphic properties of 3,5-bis-(p-n-alkoxyphenyl)isoxazole and 3,5-bis-(p-n-alkoxyphenyl)pyrazole . Mol Cryst Liq Cryst , 225 : 175 – 182 .
  • Matharu , AS and Chambers-Asman , D. 2007 . Structure-property investigation of 2- and 3-thienylacrylates bearing laterally fluorinated azobenzene moieties . Liq Cryst , 34 : 1317 – 1336 .
  • Gallardo , H , Zucco , C and Da Silva , L . 2002 . Synthesis and characterization of a new series of liquid crystal compounds derived from isoxazoles . Mol Cryst Liq Cryst , 373 : 181 – 190 .
  • Vasconcelos , UB and Merlo , AA. 2006 . Synthesis and mesomorphic behavior of new N-heterotolane liquid crystals containing a naphthyl-pyridyl framework . Synth-Stuttgart , 7 : 1141 – 1147 .
  • Aldred , MP , Vlachos , P , Dong , D , Kitney , SP , Tsoi , WC , O'Neill , M and Kelly , SM. 2005 . Heterocyclic reactive mesogens: synthesis, characterisation and mesomorphic behavior . Liq Cryst , 32 : 951 – 965 .
  • Merlo , AA , Braun , JE , Vasconcelos , U , Ely , F and Gallardo , H. 2000 . Chiral liquid crystalline m-nitrotolans and tolans: synthesis and mesomorphic properties . Liq Cryst , 27 : 657 – 663 .
  • Seed , A. 2007 . Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core . Chem Soc Rev , 36 : 2046 – 2069 .
  • Seltmann , J and Lehmann , M. 2011 . Low-melting nematic V-shaped 1,3,4-thiadiazoles – phase engineering using small substituents and mixtures of flexible chains . Liq Cryst , 38 : 407 – 422 .
  • Khazi , IAM , Gadad , AK , Lamani , RS and Bhongade , BA. 2011 . Chemistry of imidazo[2,1-b][1,3,4]thiadiazoles . Tetrahedron , 67 : 3289 – 3316 .
  • Ibrahim , DA. 2009 . Synthesis and biological evaluation of 3,6-disubstituted [1,2,4]triazolo [3,4-b][1,3,4]thiadiazole derivatives as a class of potential anti-tumor agents . Eur J Med Chem , 44 : 2776 – 2781 .
  • Gadad , AK , Mahajanshetti , CS , Nimbalkar , S and Raichurkar , A. 2000 . Synthesis and antibacterial activity of some 5-guanylhydrazone/thiocyanato-6-arylimidazo[2,1-b]-1,3,4-thiadiazole-2-sulfonamide derivatives . Eur J Med Chem , 35 : 853 – 857 .
  • Gadad , AK , Noolvi , MN and Karpoormath , RV. 2004 . Synthesis and anti-tubercular activity of a series of 2-sulfonamido/trifluoromethyl-6-substituted imidazo[2,1-b]-1,3,4-thiadiazole derivatives . Bioor Med Chem , 12 : 5651 – 5659 .
  • Gallardo , H , Conte , G , Bryk , F , Lourenco , MCS , Costa , MS and Ferreira , VF. 2007 . Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agent . J Braz Chem Soc , 18 : 1285 – 1291 .
  • Andotra , CS , Langer , TC and Kotha , A. 1997 . Synthesis and antifungal activity of some substituted 1,3,4-thiadiazolo[3,2-a]-s-triazin-5-phenyl-7-thiones and imidazo-[2,1-b]-1,3,4-thiadiazol-5-ones . J Chem Soc , 74 : 125 – 127 .
  • Noolvi , MN , Patel , HM , Kamboj , S , Kaur , A and Mann , V. 2012 . 2,6-Disubstituted imidazo[2,1-b][1,3,4]thiadiazoles: search for anticancer agents . Eur J Med Chem , 56 : 56 – 69 .
  • Khazi , IAM , Mahajanshetti , CS , Gadad , AK , Tarnalli , AD and Sultanpur , CM. 1996 . Synthesis, anticonvulsant and analgesic activities of some 6-substituted imidazo(2,1-b)-1,3,4-thiadiazole-2-sulfonamides and their 5-bromo derivatives . Arzneim Forsch - Drug Res , 46 : 949 – 952 .
  • Andreani , A , Leonia , A , Locatelli , A , Morigi , R , Rambaldi , M , Simon , WA and Senn-Bilfinger , J. 2000 . Synthesis and antisecretory activity of 6-substituted 5-cyanomethylimidazo[2,1-b]-thiazoles and 2,6-dimethyl-5-hydroxymethyl imidazo[2,1-b][1,3,4]thiadiazole . Arzneim Forsch - Drug Res , 50 : 550 – 553 .
  • Andreani , A , Rambaldi , M , Leoni , A , Locatelli , A and Bossa , R. 1996 . Potential antitumor agents. 24. Synthesis and pharmacological behavior of imidazo[2,1-b]thiazole guanylhydrazones bearing at least one chlorine . J Med Chem , 39 : 2852 – 2855 .
  • Ivashchenko , AV , Petrova , OS and Titov , VV. 1987 . 5-arylazoimidazo[2,1-b] [1,3,4]thiadiazoles - new dichroic T-dyes for LCD . Mol Cryst Liq Cryst , 145 : 25 – 29 .
  • Torgova , SI , Abolin , AG , Karamysheva , LA and Ivashchenko , AV. 1988 . Liquid-crystal imidazo-[2,1-b]-1,3,4-thiadiazoles. 1. Synthesis, mesomorphous and spectral characteristics of 2,6-di-substituted imidazo[2,1-b]-1,3,4-thiadiazoles . Zh Org Khim , 24 : 192 – 199 .
  • Torgova , SI , Abolin , AG , Roitman , KV , Karamysheva , LA and Ivashchenko , AV. 1988 . Liquid-crystal imidazo[2,1-b]-1,3,4-thiadiazoles. 2. Synthesis, mesomorphous and spectral properties of liquid-crystal 5-substituted[2,1-b]1,3,4-thiadiazoles . Zh Org Khim , 24 : 199 – 204 .
  • Torgova , SI , Shtykov , NM , Abolin , AG , Karamysheva , LA , Ivashchenko , AV and Barnik , MI. 1988 . Liquid-crystal imidazo-[2,1-b]-1,3,4-thiadizoles. 3. Synthesis and dielectric-properties of imidazo[2,1-b]-1,3,4-thiadiazoles containing polar substituents . Zh Org Khim , 24 : 1306 – 1310 .
  • Eldawy , MA , Eldine , SAS and Elbrembaly , KM. 1979 . Potential broad-spectrum anthelmintics. 4. Design, synthesis and spectral study of imidazo[2,1-b]-1,3,4-thiadiazole derivatives . Pharmazie , 34 : 144 – 147 .
  • Kolavi , G , Hegde , V and Khazi , IA. 2006 . Intramolecular amidation: synthesis of novel imidazo[2,1-b][1,3,4]thiadiazole and imidazo[2,1-b][1,3]thiazole fused diazepinones . Tetrahedron Lett , 47 : 2811 – 2814 .
  • Khazi , IAM , Mahajanshetti , CS , Gadad , AK , Tarnalli , AD and Sultanpur , CM. 1996 . Synthesis, anticonvulsant and analgesic activities of some 6-substituted imidazo(2,1-b)-1,3,4-thiadiazole-2-sulfonamides and their 5-bromo derivatives . Arzneim-Forsch/Drug Res , 46 : 949 – 952 .
  • Arbuj , SS , Waghmode , SB and Ramaswamy , AV. 2007 . Photochemical alpha-bromination of ketones using N-bromosuccinimide: a simple, mild and efficient method . Tetrahedron Lett , 48 : 1411 – 1415 .
  • Ivashchenko , AV , Torgova , SI , Karamysheva , LA and Abolin , AG. 1990 . Imidazo [2,1-b]-1,3,4-thiadiazoles - a new class of liquid-crystalline compounds . Liq Cryst , 7 : 475 – 485 .
  • Parra , M , Alderete , J , Zúñiga , C , Gallardo , H , Hidalgo , P , Vergara , J and Hernández , S. 2001 . Azo compounds and SchiOE's bases derived from 5-(4-pyridyl)-2-amino-1,3,4-thiadiazole: synthesis, mesomorphic properties and structural study by semi-empirical calculations . Liq Cryst , 28 : 1659 – 1666 .
  • Parra , M , Vergara , J , Hidalgo , P , Barbera , J and Sierra , T. 2006 . (S)-Iisoleucine and (R)-2-octanol as chiral precursors of new chiral liquid crystalline thiadiazoles: synthesis, mesomorphic and ferroelectric properties . Liq Cryst , 39 : 739 – 745 .
  • Tu , GG , Li , SH , Huang , HM , Li , G , Xiong , F , Mai , X , Zhu , HW , Kuang , BH and Xu , WF. 2008 . Novel aminopeptidase N inhibitors derived from 1,3,4-thiadiazole scaffold . Bioorg Med Chem , 16 : 6663 – 6668 .
  • Parra , ML , Elgueta , EY , Ulloa , JA , Vergara , JM and Sanchez , AI. 2012 . Columnar liquid crystals based on amino-1,3,4-thiadiazole derivatives . Liq Cryst , 39 : 917 – 925 .
  • Shafiee , A , Naimi , E , Mansobi , P , Foroumadi , A and Shekari , M. 1995 . Syntheses of substituted-oxazolo-1,3,4-thiadiazoles, 1,3,4-oxadiazoles, and 1,2,4-triazoles . J Heterocycl Chem , 32 : 1235 – 1239 .
  • Xu , LZ , Zhang , SS , Gao , HR and Jiao , K. 2003 . Studies on synthesis and biological activities of novel triazole compounds containing pyrimidine or N, N-dialkyldithiocarbamate ring . Chem Res Chin Univ , 19 : 437 – 441 .
  • Polycarpe , C , Torreilles , E , Giral , L , Babeau , A , Tinh , NH and Gasparoux , H. 1984 . Synthesis on derivatives of tetrathiafulvalene with mesamorphogenous properties . J Heterocycl Chem , 21 : 1741 – 1745 .
  • Hajipour , AR and Ruoho , AE. 2005 . Solid state deprotection of thioacetals and thioketals using 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane periodate and aluminum chloride . Org Prep Proceds Int , 37 : 298 – 303 .
  • Holshouser , MH and Kolb , M. 1986 . Facile synthesis of glycol metabolites of phenethylamino drugs . J Pharm Sci , 75 : 619 – 621 .
  • Gallardo , H , Bryk , FR , Vieira , AA , Frizon , TE , Conte , G , Souza , BS , Eccher , J and Bechtold , IH. 2009 . Optical and thermal properties of unsymmetrical liquid crystalline compounds based on isoxazole . Liq Cryst , 36 : 839 – 845 .
  • Perdew , JP , Burke , K and Ernzerhof , M. 1996 . Generalized gradient approximation made simple . Phys Rev Lett , 77 : 3865 – 3868 .
  • Schafer , A , Horn , H and Ahlrichs , R. 1992 . Fully optimized contracted Gaussian-basis sets for atoms Li to Kr . J Chem Phys , 97 : 2571 – 2577 .
  • Schafer , A , Huber , C and Ahlrichs , R. 1994 . Fully optimized contracted Gaussian-basis sets of triple zeta valence quality for atoms Li to Kr . J Chem Phys , 100 : 5829 – 5835 .
  • Gallardo , H , Conte , G , Tuzimoto , PA , Behramand , B , Molin , F , Eccher , J and Bechtold , IH. 2012 . New luminescent liquid crystals based on 2,1,3-benzothiadiazole and bent five-membered N-heterocyclic cores . Liq Cryst , 39 : 1099 – 1111 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.