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Detailed studies of perezone rearrangements

  • E. Burgueño-Tapia
  • P. Joseph-Nathan
Organische Chemie Und Biochemie

Summary

The isomerization of perezone (1) into isoperezone (2) by means of 3,4,5,6-tetrahydro-2-pyrimidinethiol afforded 6-methoxyperezone (6), the sulfide7, and the heterocycle8 as by-products. Addition of a small amount of water to the reaction system increased the yield of2 from 45 to 65%. The pathway for the formation of6,7, and8 is discussed. The reaction of2 with silica gel or withp-TsOH regioselectively yielded β-isopipitzol (3) or dihydroisoperezinone (4) in 72 and 82% yield, respectively.

Keywords

Perezone Isoperezone Rearrangement 

Detaillierte Untersuchung von Perezon-Umlagerungen

Zusammenfassung

Die Isomerisierung von Perezon (1) zu Isoperezon (2) mit 3,4,5,6-Tetrahydro-2-pyrimidinthiol ergab 6-Methoxyperezon (6), das Sulfid7 und den Heterocyclus8 als Nebenprodukte. Zugabe einer geringen Menge Wasser zum Reaktionsgemisch erhöhte die Ausbeute an2 von 45 auf 65%. Der Mechanismus der Bildung von6,7 und8 wird diskutiert. Reaktion von2 mit Kieselgel oderp-TsOH führte regioselektiv mit 72 bzw. 82% Ausbeute zu β-Isopipitzol (3) oder Dihydroisoperezinon (4).

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Copyright information

© Springer-Verlag 1997

Authors and Affiliations

  • E. Burgueño-Tapia
    • 1
  • P. Joseph-Nathan
    • 1
  1. 1.Departamento de Química, Centro de Investigación y de Estudios AvanzadosInstituto Politécnico NacionalMéxico D.F.México

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