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Original Articles

Novel Regioselective Formation of S- and N-Hydroxyl-Alkyls of 5-(3-Chlorobenzo[b]Thien-2-yl)-3-Mercapto-4H-1,2,4-Triazole and A Facile Synthesis of Triazolo-Thiazoles and Thiazolo-Triazoles. Role of Catalyst and Microwave

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Pages 437-451 | Received 11 Aug 2006, Accepted 15 Mar 2007, Published online: 19 Jun 2007

REFERENCES

  • Campaigne , E. 1984 . Comprehensive Heterocyclic Chemistry Edited by: Katritzky , A. R. , Rees , C. W. , Kliegman , RM and Arvin , AM . Vol. 4 , 863 – 934 . Pergamon
  • Marcel , D. and Etienne , V. 1974 . Antiarthritic benzo[b]thien-2-ylacetic acid and esters. German Offen . Chem. Abstr , 80 : 59856 1972, 2,328,060
  • Connor , D. T. , Cetenko , W. A. , Mullican , M. D. , Sorenson , R. J. , Unangst , P. C. , Weikert , R. J. , Adolphson , R. L. , Kennedy , J. A. , Thueson , D. O. , Wright , C. D. and Conroy , M. C. 1992 . Novel benzothiophene-, benzofuran-, and naphthalenecarboxamidotetrazoles as potential antiallergy agents . J. Med. Chem. , 35 : 958 – 965 .
  • Graham , S. L. , Shepard , K. L. , Anderson , P. S. , Baldwin , J. J. , Best , D. B. , Christy , M. E. , Freedman , M. B. , Gautheron , P. , Habecker , C. N. , Hoffman , J. M. , Lyle , P. A. , Michelson , S. R. , Ponticello , G. S. , Robb , C. M. , Schwam , H. , Smith , A. M. , Smith , R. L. , Sondey , J. M. , Strohmaier , K. M. , Sugrue , M. F. and Varga , S. L. 1989 . Topically active carbonic anhydrase inhibitors. Benzo[b]thiophenesulfonamide derivatives with ocular hypotensive activity . J. Med. Chem. , 32 : 2548 – 2554 .
  • Jones , C. D. , Jevnikar , M. G. , Pike , A. J. , Peters , M. K. , Black , L. J. , Thompson , A. R. , Falcone , J. F. and Clements , J. A. 1984 . Antiestrogens. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[b]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride (LY156758), a remarkably effective estrogen antagonist with only minimal instrinsic estrogenicity . J. Med. Chem. , 27 : 1057 – 1066 .
  • Schmid , C. R. , Glasebrook , A. L. , Misner , J. W. and Stephenson , G. A. 1999 . Synthesis and biological activity of trans-2,3-dihydroraloxifene . Bioorg. Medic. Chem. Lett. , 9 : 1137 – 1140 .
  • Grese , T. A. and Dodge , J. A. 1996 . Annual Reports in Medicinal Chemistry , Edited by: Bristol , J. A. Vol. 31 , 181 – 190 . New York : Academic .
  • Tozkoparan , B. , Gökhan , N. , Aktay , G. , Yeşilada , E. and Ertan , M. 2000 . 6-Benzylidenethiazolo[3,2-b]-1,2,4-triazole-5(6H)-one substituted with ibuprofen: synthesis, characterization and evaluation of anti-inflammatory activity . Eur. J. Med. Chem. , 34 : 743 – 750 .
  • Demirbas , N. , Ugurluoglu , R. and Demirbas , A. 2002 . Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents . Bioorg. Med. Chem. , 10 : 3717 – 3723 .
  • Emilsson , H. , Salender , H. and Gaarder , J. 1985 . Synthesis and antihypertensive activity of 3-amino-4-(aryledeneamino)-4H-1,2,4-triazoles . Eur. J. Med. Chem. Chimi. Ther. , 21 : 333 – 337 .
  • Kritsanida , M. , Mouroutsou , A. , Marakos , P. and Pouli , N. 2002 . Papakonstantinou-Garoufalias, S.; Pannecouque, C.; Witvouw, M.; De Clercq, E. Synthesis and antiviral activity evaluation of some new 6-substituted 3-(1-adamantyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles . IL Farmaco , 57 : 253 – 257 .
  • Griffin , D. A. and Mannion , S. K. 1987 . Preparation of substituted triazolylbutanoates as plant growth regulators . Chemi. Abstr , 106 : 98120u European Patent 1986, 199,474
  • Turan-Zitouni , G. , Kaplancikli , Z. A. , Erol , K. and Kilic , F. S. 1999 . Synthesis and analgesic activity of some triazoles and triazolothiadiazines . Il Farmaco , 54 : 218 – 223 .
  • Heubach , G. , Sachse , H. and Buerstell , H. 1980 . 1,2,4-Triazole derivatives. German Offen 1978, 2,826,760; . Chem. Abstr. t , 92 : 181200 h
  • Murabayashi , A. , Masuko , M. , Niikawa , M. , Shirane , N. , Futura , T. , Hayashi , Y. and Makisumi , Y. 1991 . Antifungal and plant growth inhibitory activities of stereo and optical isomers of 2-triazolylcycloalkanol derivatives . J. Pest. Sci. , 16 : 419 – 427 .
  • The Merck Index . 2001 . 3737 USA, NJ : Whitehouse Station .
  • Vogel , G. W. and Morris , D. 1992 . The effects of estazolam on sleep, performance, and memory: A long-term sleep laboratory study of elderly insomniacs . J. Clin. Pharmacol. , 32 : 647 – 651 .
  • The Merck Index . 2001 . 320 USA, NJ : Whitehouse Station .
  • The Merck Index . 2001 . 8324 USA, NJ : Whitehouse Station .
  • Tsukuda , T. , Shiratori , Y. , Watanabe , M. , Ontsuka , H. , Hattori , K. , Shirai , M. and Shimma , N. 1998 . Modeling, synthesis and biological activity of novel antifungal agents . Bioorg. Med. Chem. Lett. , 8 : 1819 – 1824 .
  • El Ashry , E.S. H. and El Kilany , Y. 1996 . Acyclonucleosides: Part 1 . Seco-nucleosides. Adv. Heterocyc. Chem , 67 : 391 – 438 .
  • El Ashry , E. S.H. and El Kilany , Y. 1997 . Acyclonucleosides: Part 2. . Diseco-nucleosides. Adv. Heterocyc. Chem , 68 : 1 – 88 .
  • El Ashry , E. S.H. and El Kilany , Y. 1998 . Acyclonucleosides: Part 3 . Tri-tetra-, and pentaseco-nucleosides Adv. Heterocyc. Chem , 9 : 129 – 215 .
  • Shaeffer , H. J. , Beauchamp , L. , de Miranda , P. , Elion , G. B. , Bauer , D. J. and Collins , P. 1978 . 9-(2-Hydroxyethoxymethyl) guanine activity against viruses of the herpes group . Nature (London) , 272 : 583 – 585 .
  • Perigaud , C. , Gosselin , G. and Imbach , J. L. 1992 . Stereospecific synthesis of chiral acyclic analogs of guanosine . Bioorg. Med. Chem. Lett. , 2 : 677 – 680 .
  • Abushanab , E. 1993 . Nucleosides and Nucleotides as Antitumor and Antiviral Agents , Edited by: Chu , C. K. and Baker , D. C. 159 – 171 . New York : Plenum Press .
  • Garg , R. , Gupta , S. P. , Gao , H. , Babu , M. S. , Debnath , A. K. and Hansch , C. 1999 . Comparative quantitative structure-activity relationship studies on anti-HIV drugs . Chem. Rev. , 99 : 3525 – 3601 .
  • El-Essawy , F. A. 2005 . Synthesis of novel acyclonucleosides analogs of pyridothienopyrimidine as antiviral agents . Nucleosides Nucleotides Nucleic Acids , 24 : 1265 – 1276 .
  • Oh , C.-H. , Baek , T.-R. and Hong , J. H. 2005 . Concise synthesis and antiviral activity of novel unsaturated acyclic pyrimidine nucleosides . Nucleosides Nucleotides Nucleic Acids , 24 : 153 – 160 .
  • Eger , K. , Klünder , E. M. and Schmidt , M. 1994 . Synthesis of new acyclic pyrimidines nucleoside analogs as potential antiviral drugs . J. Med. Chem. , 37 : 3057 – 3061 .
  • Lazrek , H. B. , Taourirte , M. , Oulih , T. , Barascut , J. L. , Imbach , J. L. , Pannecouque , C. , Witrouw , M. and De Clercq , E. 2001 . Synthesis and anti-HIV activity of new modified 1,2,3-triazole acyclonucleosides . Nucleosides Nucleotides Nucleic Acids , 20 : 1949 – 1960 .
  • Lucero , B.d’ A. , Gomes , C. R.B. , Frugulhetti , I. C.P.P. , Faro , L. V. , Alvarenga , L. , De Souza , M. C.B.V. , De Souza , T. M.L. and Ferreira , V. F. 2006 . Synthesis and anti-HSV-1 activity of quinolonic acyclovir analogues . Bioorg. Med. Chem. Lett. , 16 : 1010 – 1013 .
  • Hakimelahi , G. H. , Ly , T. W. , Moosavi-Movahedi , A. A. , Jain , M. L. , Zakerinia , M. , Davari , H. , Mei , H.-C. , Sambaiah , T. , Moshfegh , A. A. and Hakimelahi , S. 2001 . Design, synthesis, and biological evaluation of novel nucleoside and nucleotide analogues as agents against DNA viruses and/or retroviruses . J. Med. Chem. , 44 : 3710 – 3720 .
  • Chu , C. K. and Cutler , S. J. 1986 . Chemistry and antiviral activities of acyclonucleosides . J. Heterocyc. Chem. , 23 : 289 – 319 .
  • Chu , C. K. and Jungjin , S. 1986 . Acyclopyrimidine C-nucleosides: synthesis of 5-[2,3-dihydroxy-1-propoxy)methyl]pyrimidines . J. Heterocyc. Chem. , 23 : 1621 – 1624 .
  • Abdel-Rahman , A.-H. and El Ashry , E. S.H. 2002 . Efficient synthesis of 5-hydroxymethyl pyrimidines and their nucleosides using microwave irradiation . Synlett , : 2043 – 2044 .
  • Abdel Hamid , H. M. , Ramadan , E. , Hagar , M. and El Ashry , E. S.H. 2004 . Synthesis of aryloxyacetic acids, esters and hydrazides assisted by microwave irradiation . Synth. Comm. , 34 : 377 – 382 .
  • El Ashry , E. S.H. , Ramadan , E. , Abdel Hamid , H. M. and Hagar , M. 2004 . Synthesis of azalactones, phenylpyruvic acid and 1,2,4-triazine derivatives under microwave irradiation . Lett. Org. Chem. , 2 : 415 – 418 .
  • El Ashry , E. S.H. , Ramadan , E. , Abdel Hamid , H. and Haggar , M. 2005 . Microwave irradiation for enhancing the synthesis of quinoline derivatives from isatin . Synth. Comm. , 35 : 2243 – 2250 .
  • El Ashry , E. S.H. , Ramadan , E. , Abdel-Hamid , H. and Hagar , M. 2005 . Microwave irradiation for enhancing the regioselective synthesis of 6H-indolo[2,3-b]quinoxaline . J. Chem. Res. , : 229 – 232 .
  • El Ashry , E. S.H. , Ramadan , E. , Abdel-Hamid , H. and Hagar , M. 2004 . Microwave irradiation for accelerating the synthesis of 1,2,4-triazino[5,6-b]indole-2-thiols and their derivatives from isatin and 5-chloroisatin . Synlett , : 723 – 725 .
  • El Ashry , E. S.H. , Awad , L. F. , Abdel-Hamid , H. and Atta , A. I. 2005 . Synthesis of interglycosidically S-linked 1-thio-oligosaccharides under microwave irradiation . J. Carb. Chem. , 24 : 745 – 753 .
  • El Ashry , E. S.H. , Awad , L. F. , Abdel-Hamid , H. and Atta , A. I. 2005 . Microwave-assisted organic synthesis of 3-(D-gluco-pentitol-1-yl)-1H-1,2,4-triazole . Nucleosides Nucleotides Nucleic Acids , 25 : 325 – 335 .
  • El Ashry , E. S.H. , Awad , L. F. , Abdel-Hamid , H. and Atta , A. I. 2005 . Int. Soc. for Nucleosides Nucleotides Nucleic Acids XVIInt. Round Table, Minneaoplis, Minnesota, USA, (2004) PS. Microwave Irradiation for accelerating the Synthesis of Acyclonucleosides of 1,2,4-triazole . Nucleosides Nucleotides Nucleic Acids , 24 : 427 – 429 .
  • El Ashry , E. S.H. , Rashed , N. , Awad , L. F. , Ramadan , E. and Abdel-Mageed , S. M. 2007 . Rezki, N. MAOS Versus conventional synthesis of 4,5-di- and 3,4,5-triphenylimidazole-2-thione and their derivatives . ARKIVOC ,
  • El Ashry , E. S.H. , Kassem , A. A. , Abdel-Hamid , H. , Louis , F. F. , Khattab , Sh. A.N. and Aouad , M. R. 2006 . Synthesis and alkylation of 5-(3-chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole-3-thiol under classical and microwave conditions. AM1 Semiemperical calculations for investigating the regioselectivity of alkylation . J. Heterocyc. Chem. , 43 : 1421 – 1429 .
  • Li , Z. , Wang , Z.-Y. , Zhu , W. , Xing , Y.-L. and Zhao , Y.-L. 2005 . CeCl3.7H2O-KI-Catalyzed, environmentally friendly synthesis of N,N′-disubstituted ureas in water under microwave irradiation . Synth. Comm. , 35 : 2325 – 2331 .
  • Santagada , V. , Frecentese , F. , Perissutti , E. , Cirillo , D. , Terracciano , S. and Caliendo , G. 2004 . A suitable 1,2,4-oxadiazoles synthesis by microwave irradiation . Bioorg. Med. Chem. Lett. , 14 : 4491 – 4493 .
  • Galema , S. A. 1997 . Microwave chemistry . Chem. Soc. Rev. , 26 : 233 – 238 .
  • Mingos , D. and Whittaker , M. P.A. 1997 . “ Microwave Dielectric Heating Effects in Chemical Synthesis in Chemistry under Extreme or Non Classical Conditions ” . Edited by: Eldik , R. V. and Hubbark , C. D. 479 John Wiley & Sons Inc .
  • Gabriel , C. , Gabriel , S. , Grant , E. H. , Halstead , B. S.J. and Mingos , D. M.P. 1998 . Dielectric parameters relevant to microwave dielectric heating . Chem. Soc. Rev. , 27 : 213 – 223 .
  • Perrux , L. and Loupy , A. 2001 . A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations . Tetrahedron , 57 : 9199 – 9223 .
  • Hamelin , J. , Bazureau , J. P. and Texier-Boullet , F. 2002 . “ Microwave in Organic Synthesis ” . Edited by: Loupy , A. 253 Wiley-VCH .
  • El Ashry , E. S.H. , Ramadan , E. , Kassem , A. A. and Haggar , M. 2005 . Microwave irradiation for accelerating organic reactions. Part 1: Three, four and five membered heterocyclese . Adv. Heterocyc. Chem. , 88 : 1 – 110 .
  • El Ashry , E. S.H. , Kassem , A. A. and Ramadan , E. 2006 . Microwave irradiation for accelerating organic reactions. Part 2: Six, seven fused and spiro heterocyclic ring Systems . Adv. Heterocyc. Chem , 90 : 1 – 127 .
  • El Ashry , E. S.H. and Kassem , A. A. 2006 . Account of microwave irradiation for accelerating organic reactions . ARKIVOC , ix : 1 – 15 .
  • Devi , I. and Bhuyan , P. J. 2005 . An expedient method for the synthesis of 6-substituted uracils under microwave irradiation in a solvent-free medium . Tetrahedron Lett. , 46 : 5727 – 5729 .
  • Dhakshinamoorthy , A. and Pitchumani , K. 2005 . Facile clay-induced fischer indole synthesis: a new approach to synthesis of 1,2,3,4-tetrahydrocarbazole and indoles . Appl. Catal. A , 292 : 305 – 311 .
  • Regnier , T. and Lavastre , O. 2006 . General and enviromentally friendly synthesis of heterocyclic multidentate molecules based on microwave-assisted heating protocol . Tetrahedron , 62 : 155 – 159 .
  • Yadav , L.D.S. , Yadav , B. S. and Dubey , S. 2004 . Mineral supported syntheses of benzoxazine-2-thiones under microwave irradiation . Tetrahedron , 60 : 131 – 136 .
  • El Ashry , E. S.H. , Rashed , N. and Awad , L. F. 2001 . Abdel-Rahman, A.A.-H.; Rasheed, H.A. Synthesis of new 7-alkylated theophyllines by chemical modification of dyphylline. Journal of Chemical Research (S) 2001, 2, 129–130 . J. Chem. Res. (M) , : 440 – 450 .
  • El Ashry , E. S.H. , Abdel Rahman , A. A.-H. , Rashed , N. and Rasheed , H. A. 1999 . Homoacylovir analogues of unnatural bases and their activity against hepatitis B virus . Pharmazie , 54 : 893 – 897 .
  • El Ashry , E.S.H. , Abdel-Rahman , A.A.H. , Rashed , N. and Rasheed , H. A. 1999 . Synthesis and anti-hepatitis B virus activity of some 2,3-dihydroxyprop-1-yl unnatural hetaryls . Arch. Pharm. Med. Chem. , 332 : 327 – 330 .
  • Mitsunobu , O. 1981 . The use of diethyl azodicaboxylate and triphenylphosphine in synthesis and transformation of natural products . Synthesis , 1–28 : 1 – 28 .
  • Janeba , Z. , Holy , A. and Masojidkova , M. 2000 . Synthesis of acyclic nucleoside and nucleotide analogs derived from 6-amino-7H-purine-8(9H)-thione . Coll. Czech Chem. Comm. , 65 : 1698 – 1712 .

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