Straightforward Access to Ethyl 3-Aminofuropyridine-2-carboxylates from 1-Chloro-2-cyano- or 1-Hydroxy-2-cyano-Substituted Pyridines

Thomas Cailly; Stéphane Lemaître; Frédéric Fabis; Sylvain Rault

doi:10.1055/s-2007-990810

PAPER

Straightforward Access to Ethyl 3-Aminofuropyridine-2-carboxylates from 1-Chloro-2-cyano- or 1-Hydroxy-2-cyano-Substituted Pyridines

Thomas Cailly, Stéphane Lemaître, Frédéric Fabis, Sylvain Rault*
Centre d’Etudes et de Recherche sur le Médicament de Normandie, U.F.R. des Sciences Pharmaceutiques, Université de Caen Basse-Normandie, 5 rue Vaubénard, 14032 Caen Cedex, France
Fax: +33(2)31931188; e-Mail: sylvain.rault@unicaen.fr;

Abstract

All articles of this category

Abstract

The conditions of the synthesis of the four regioisomers of ethyl 3-aminofuropyridine-2-carboxylate are described and discussed in detail. The starting materials are either 1-chloro-2-cyanopyridines or 1-cyano-2-hydroxypyridines.

Key words

fused-ring systems - cyclizations - nitriles - aryl alcohols - nucleophilic aromatic substitutions

Full Text

References

1a Gogerty JH. Griot RG. Habeck D. Iorio LC. Houlihan WJ. J. Med. Chem. 1977, 20: 952

1b Peet NP. Sunder S. J. Heterocycl. Chem. 1977, 14: 561

1c Hirayama F. Koshio H. Katayama N. Ishihara T. Kaizawa H. Taniuchi Y. Sato K. Sakai-Moritani Y. Kaku S. Kurihara H. Kawasaki T. Matsumoto Y. Sakamoto S. Tsukamoto S. Bioorg. Med. Chem. 2003, 11: 367

2a Hennequin LF. Allen J. Breed J. Curwen J. Fennell M. Green TP. Lambert van der Brempt C. Morgentin R. Norman RA. Olivier A. Otterbein L. Plé PA. Warin N. Costello G. J. Med. Chem. 2006, 49: 6465

2b Desroses M. Laconde G. Depreux P. Henichart JP. Org. Prep. Proced. Int. 2004, 36: 445

2c Wright SW. Carlo AA. Carty MD. Danley DE. Hageman DL. Karam GA. Levy CB. Mansour MN. Mathiowetz AM. McClure LD. Nestor NB. McPherson RK. Pandit J. Pustilnik LR. Schulte GK. Soeller WC. Treadway JL. Wang IK. Bauer PH. J. Med. Chem. 2002, 45: 3865

3a Barker JM. Huddleston PR. Holmes D. J. Chem. Res., Synop. 1986, 5: 155

3b Elliott RL. O’Hanlon PJ. Rogers NH. Tetrahedron 1987, 43: 3295

3c Danswan G. Kennewell PD. Tully WRJ. Heterocycl. Chem. 1989, 26: 293

4 Prunier H. Rault S. Lancelot JC. Robba M. Renard P. Delagrange P. Pfeiffer B. Caignard DH. Misslin R. Guardiola-Lemaitre B. Hamon M. J. Med. Chem. 1997, 40: 1808

5 Hinschberger A. Butt S. Lelong V. Boulouard M. Dumuis A. Dauphin F. Bureau R. Pfeiffer B. Renard P. Rault S. J. Med. Chem. 2003, 46: 138

6 Rochais C. Lisowski V. Dallemagne P. Rault S. Bioorg. Med. Chem. 2006, 14: 8162

7 Lisowski V. Leonce S. Kraus-Berthier L. Sopkova-de Oliveira Santos J. Pierre A. Atassi G. Caignard DH. Renard P. Rault S. J. Med. Chem. 2004, 47: 1448

8a Dunn AD. Norrie R. J. Prakt. Chem. 1996, 338: 663

8b Zheng GZ. Bhatia P. Daanen J. Kolasa T. Patel M. Latshaw S. El Kouhen OF. Chang R. Uchic ME. Miller L. Nakane M. Lehto SG. Honore MP. Moreland RB. Brioni JD. Stewart AO. J. Med. Chem. 2005, 48: 7374

8c Sauter F. Froehlich J. Ahmed EK. Monatsh. Chem. 1995, 26: 945

8d Narsaiah B. Sivaprasad A. Venkataratnam RV. J. Fluorine Chem. 1994, 69: 139

8e Wagner G. Prantz J. Pharmazie 1993, 48: 250

8f Kamal El-Dean AM. Abdel Hafez AA. Attallah AA. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 46: 1

8g Gewald K. Jaensch HJ. J. Prakt. Chem. 2004, 318: 313

9 Cho YH. Park JH. Tetrahedron Lett. 1997, 38: 8331

10 Cailly T. Fabis F. Lemaître S. Bouillon A. Rault S. Tetrahedron Lett. 2005, 46: 135

11 Cailly T. Fabis F. Lemaître S. Bouillon A. Sopkova J. Rault S. Synlett 2006, 53

12 Hansen HM. Lysén M. Begtrup M. Kristensen J. Tetrahedron 2005, 61: 9955

13 Voisin AS. Bouillon A. Lancelot JC. Rault S. Tetrahedron 2005, 61: 1427

14 Webb KS. Levy D. Tetrahedron Lett. 1995, 36: 5117

15 Sangapure SS. Agasimundin YS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1975, 14: 688