Synthesis of 3-substituted-1-methyl-1H-thieno[2,3-c]pyrazoles

Synthetic Communications

Volumn 38, Issue 5, 2008, Pages 674-683

  Toto, Patrick ^a   Chenault, Jacques ^a   Hakmaoui, Ahmed El ^b   Akssira, Mohamed ^b   Guillaumet, Gerald ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b HASSAN II UNIVERSITY OF CASABLANCA   (Morocco)

Author keywords

Cyclization; Pyrazoles; Thienopyrazoles

Indexed keywords

1 METHYL 1H THIENO[2,3 C]PYRAZOLE DERIVATIVE; 3 AMINO 1H PYRAZOLE 4 CARBOXYLIC ACID ETHYL ESTER; BROMINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; BROMINATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 39049090386     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701818578     Document Type: Article

References (17)

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