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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 5
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Original Articles

Synthesis of 3‐Substituted‐1‐methyl‐1H‐thieno[2,3‐c]pyrazoles

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Pages 674-683 | Received 27 Jun 2007, Published online: 15 Feb 2008

References

  • Campos , P. L. , Anon , E. , Carmen Malo , M. and Rodriguez , M. A. 1999 . A versatile synthesis of pyrrolo‐, furo‐ and thienopyridines via photocyclization of 3‐amino‐2‐alkene imines in an acid medium . Tetrahedron , 55 : 14079 – 14088 .
  • Labelle , M. , Gareau , Y. , DufTesne , C. , Lau , C. K. , Belley , M. , Jones , T. R. , Leblanc , Y. , McAuliffe , M. , McFarlane , C. S. , Metters , K. M. , Quimet , N. , Perrier , H. , Rochette , C. , Sawyer , N. , Slipetz , D. , Xiimg , Y. B. , Wang , Z. , Pickett , C. B. , Ford‐Hutchinson , A. W. , Young , R. N. and Zamboni , R. 1995 . Discovery of L‐740,515, a potent thienopyridine cysLT1 receptor (LTD4 receptor) antagonist . Bioorg. Med. Chem. Lett. , 21 : 2551 – 2556 .
  • Russell , R. K. , Press , J. B. , Rampulla , R. A. , McNally , L. L. , Falotico , R. , Keiser , L. A. , Bright , D. A. and Tobia , A. 1988 . Thienopyrimidinedione derivatives as potential antihypertensive agents . J. Med. Chem. , 31 : 1786 – 1793 .
  • Ife , R. J. , Brown , T. H. , Blurton , P. , Keeling , D. J. , Leach , C. A. , Meeson , M. L. , Parsons , M. E. and Theobald , C. L. 1995 . Reversible inhibitors of the gastric (H+/K+)‐ATPase, 5: Substituted 2,4‐diaminoquinazolines and thienopyrimidines . J. Med. Chem. , 38 : 2763 – 2773 .
  • Modica , M. , Santagati , M. , Guccione , S. , Russo , F. , Cagnotto , A. , Goegan , M. and Mennini , T. 2000 . Design, synthesis and binding properties of novel and selective 5‐HT3 and 5‐HT4 receptor ligands. Eur . J. Med. Chem. , 35 : 1065 – 1079 .
  • Welch , M. and Phillips , R. S. 1999 . Improved syntheses of [3,2‐b] and [3,2‐b] fused selenolo and thienopyrroles, and of furo[3,2‐b]pyrrole . Heterocycl. Commun. , 5 : 305 – 310 .
  • Blair , B. B. , Marona‐Lewicka , D. , Kanthasamy , A. , Lucaites , V. L. , Nelson , D. L. and Nichols , D. E. 1999 . Thieno[3,2‐b] and thieno[2,3‐b]pyrrole bioisosteric analogues of the hallucinogen and serotonin agonist N,N‐dimethyltryptamine . J. Med. Chem. , 42 : 1106 – 1111 .
  • Sommen , G. , Comel , A. and Kirsch , G. 2001 . An easy access to variously substituted thieno[2,3‐b]pyrroles by using isothiocyanates . Synlett. , : 1731 – 1734 .
  • Sommen , G. , Comel , A. and Kirsch , G. 2003 . Preparation of thieno[2,3‐b]pyrroles starting from ketene‐N,S‐acetals . Tetrahedron , 59 : 1557 – 1564 .
  • Fiesselmann , H. and Thoma , F. 1956 . The preparation of 3‐hydroxy‐2‐thiophenecarboxylic esters from 3‐oxo acid esters . Chem. Ber. , 89 : 1907 – 1912 .
  • Donoso , R. , Jordan de Urries , P. and Lissavetzky , J. 1992 . Synthesis of [b]‐condensed alkyl 3‐hydroxythiophene‐2‐carboxylates . Synthesis , : 526 – 528 .
  • Cottineau , B. , Chenault , J. and Guillaumet , G. 2006 . New synthesis of 3‐methoxy‐4‐substituted pyrazole derivatives . Tetrahedron Lett. , 47 : 817 – 820 .
  • Cottineau , B. , Renaux , S. , Chenault , J. and Guillaumet , G. 2005 . New synthesis of pyrazolyl‐1,3,4‐oxadiazole and 1,3,4‐oxadiazoline derivatives . Lett. Org. Chem. , 2 : 398 – 403 .
  • Nagahara , K. , Takagi , K. and Ueda , T. 1976 . Reaction of ethoxymethylenemalono‐nitrile with hydrazine hydrate . Chem. Pharm. Bull. , 24 : 2880 – 2882 .
  • Morimoto , K. , Sato , T. , Yamamoto , S. and Takeuchi , H. 1997 . Synthesis of halosulfuron‐methyl via selective chlorination at the 3‐ and/or 5‐position of pyrazole‐4‐carboxylates . J. Heterocycl. Chem. , 34 : 537 – 540 .
  • Holzer , W. and Seiringer , G. 1993 . N1‐Substituted ethyl 4‐pyrazolecarboxylates: synthesis and spectroscopic investigations . J. Heterocycl. Chem. , 30 : 865 – 872 .
  • Bertz , S. H. , Dabbagh , G. and Cotte , P. 1982 . New preparations of ethyl 3,3‐diethoxypropionate and ethoxycarbonyl‐malondialdehyde: Copper(I) catalyzed acetal formation from a conjugated triple bond . J. Org. Chem. , 47 : 2216 – 2217 .

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