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Paper | Regular issue | Vol 34, No. 10, 1992, pp.1885-1895
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6078
Synthesis and Stereochemistry of Tropane 6-Spiro-hydantoins

Mercedes Villacampa,* Manuel Martínez, Gregorio González-Trigo, and Mónica M. Söllhuber

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain

Abstract

The synthesis of several representatives of the previously unknown N-alkyl-nortropane-6-spirohydantoin ring system by Bucherer-Bergs reaction of 8-alkyl-8-azabicyclo[3.2.1]octan-6-ones is described. 3-Oxo derivatives of the parent structure were also prepared. The stereochemical outcome of the Bucherer-Bergs reaction is discussed on the basis of 1H-nmr and 13C-nmr data.