Efficient Synthesis of 3-Bromo-2-[(N-substituted)amino]pyridines and their Hetarynic Cyclization

Irina-Claudia Grig-Alexa; Adriana-Luminita Finaru; Lucia Ivan; Paul Caubère; Gérald Guillaumet

doi:10.1055/s-2006-926311

PAPER

Efficient Synthesis of 3-Bromo-2-[(N-substituted)amino]pyridines and their Hetarynic Cyclization

Irina-Claudia Grig-Alexa^a,b, Adriana-Luminita Finaru^b, Lucia Ivan^c, Paul Caubère^a, Gérald Guillaumet*^a
^a Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France
e-Mail: gerald.guillaumet@univ-orleans.fr;
^b Laboratorul de Sinteza Organica si Analiza Structurala, Universitatea Bacau, 157, Calea Marasesti, 600115 Bacau, Romania
^c Laboratorul de Sinteza Organica, Facultatea de Chimie, Universitatea Bucuresti, Bd. Elisabeta, Bucuresti, Romania

Abstract

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Abstract

A variety of 3-bromo-2-[(N-substituted)amino]pyridines were obtained via two convenient methods and were used in the hetarynic synthesis of the corresponding N-substituted dihydrodipyridopyrazines.

Key words

3-bromo-2-[(N-substituted)amino]pyridines - dihydrodipyridopyrazines - hetarynic cyclization

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References

1 Blanchard S. Rodriguez I. Kuehm-Caubère C. Renard P. Pfeiffer B. Guillaumet G. Caubère P. Tetrahedron 2002, 58: 3513

2a Caubère P, Guillaumet G, Rodriguez I, Vinter-Pasquier K, Kuehm-Caubère C, Blanchard S, Atassi G, Pierre A, Pfeiffer B, and Renard PP. inventors; Eur. Pat. Appl. EP 96986. ; Chem. Abstr. 2000, 132, 22978

2b Blanchard S. Rodriguez I. Tardy C. Baldeyrou B. Bailly C. Colson P. Houssier C. Léonce S. Kraus-Berthier L. Pfeiffer B. Renard P. Pierre A. Caubère P. Guillaumet G. J. Med. Chem. 2004, 47: 978

3a Caubère P. Acc. Chem. Res. 1974, 7: 301

3b Caubère P. Top. Curr. Chem. 1978, 73: 50

3c Caubère P. Rev. Heteroat. Chem. 1991, 4: 78

3d Caubère P. Chem. Rev. 1993, 93: 2317

3e Caubère P. J. Chin. Chem. Soc. (Taipei) 1998, 45: 451 ; and references cited therein

4a Flouzat C. Guillaumet G. Synthesis 1990, 64

4b Viscardi G. Savarino P. Barni E. Carpignano R. J. Heterocycl. Chem. 1991, 27: 1825

5 Brown HC. Heim P. J. Org. Chem. 1973, 38: 912

6a Blanchard S. Rodriguez I. Caubère P. Guillaumet G. Synlett 2002, 1356

6b Grig-Alexa IC. Finaru AL. Ivan L. Caubère P. Guillaumet G. Tetrahedron Lett. 2004, 45: 2343

7 Turner JA. J. Org. Chem. 1983, 48: 3401

8 Major RT. Peterson LH. J. Org. Chem. 1957, 22: 579