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Synlett 2004(7): 1123-1139  
DOI: 10.1055/s-2004-822894
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© Georg Thieme Verlag Stuttgart · New York

New Pathways Towards Pyridazino-Fused Ring Systems

Péter Mátyus*a, Bert U.W. Maes*b, Zsuzsanna Riedl*c, György Hajósc, Guy L.F. Lemièreb, Pál Tapolcsányia, Katrien Monsieursb, Olivér Éliása, Roger A. Dommisseb, Gábor Krajsovszkya
a Department of Organic Chemistry, Semmelweis University, 1092 Budapest, Hõgyes E. u. 7., Hungary
Fax: +36(1)2170851; e-Mail: matypet@szerves.sote.hu;
b Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp, Belgium
Fax: +32(3)2653233; e-Mail: bert.maes@ua.ac.be;
c Chemical Research Center, Institute of Chemistry, Hungarian Academy of Sciences, 1525 Budapest, P.O. Box 17, Hungary
Fax: +36(1)3257683; e-Mail: zriedl@chemres.hu;
Further Information

Publication History

Received 5 December 2003
Publication Date:
25 March 2004 (online)

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Abstract

Novel, efficient synthetic pathways were developed for the synthesis of a variety of pyridazino-fused polycyclic ring systems not easily accessible by other routes. The strategy is based on the sequential or one-pot combinations of a palladium catalyzed C-C bond forming process (Suzuki or Heck-type reaction) and a C-X (X = N, O) or another C-C bond forming reaction (for C-X: nucleophilic substitution, condensation, lactonization, nitrene C-H insertion, Buchwald-Hartwig amination; for C-C: Pschorr reaction, Heck-type reaction). Some of these methodologies have also been extended to the preparation of several diazino-fused ring systems.

1 Introduction

2 Results

2.1 Suzuki Reaction of Halopyridazinones

2.2 Suzuki Reaction and Nitrene Insertion or Azo-Coupling

2.3 Suzuki Reaction and Nucleophilic Substitution or
Condensation ­Reaction

2.4 Suzuki Reaction and Heck-Type Arylation

2.5 Suzuki Reaction and Pschorr Reaction

2.6 Nucleophilic Substitution Reaction and Heck-Type ­Arylation

2.7 Buchwald-Hartwig Reaction of Halopyridazinones

2.8 Buchwald-Hartwig Reaction and Heck-Type Arylation

3 Conclusion

4 References

Key words

pyridazine - palladium-catalyzed reaction - pyridazino-fused ring systems - diazino-fused ring systems

15

Éliás, O.; Tapolcsányi, P.; Mátyus, P. et al., unpublished results.