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Adamantane derivatives IV: Unexpected debenzylation on ring closure of 1-(1-adamantylcarbonyl)-4-benzylthiosemicarbazide with sulphuric acid

Adamantan Derivate, 4. Mitt.: Unerwartete Debenzylierung bei der Cyclisierung von 1-(1-Adamantylcarbonyl)-4-benzylthiosemicarbazid mit Schwefelsäure

  • Organische Chemie Und Biochemie
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Summary

Cyclization of 1-(1-adamantylcarbonyl)-4-substituted thiosemicarbazides2a–e with sulphuric acid at ambient temperature or by heating with phosphorus oxychloride yielded the corresponding 2-(1-adamantyl)-5-amino-1,3,4-thiadiazoles3a–e. Cyclization of 1-(1-adamantylcarbonyl)-4-benzylthiosemicarbazide2f with sulphuric acid gave the debenzylated product 2-(1-adamantyl)-5-amino-1,3,4-thiadiazole4. On the other hand, cyclization of2f using phosphorus oxychloride yielded 2-(1-adamantyl)-5-benzylamino-1,3,4-thiadiazole3f.

Zusammenfassung

Die 4-substituierten 1-(1-Adamantylcarbonyl)-thiosemicarbazide2a–e cyclisieren mit Schwefelsäure bei Raumtemperatur oder durch Erhitzen mit Phosphoroxytrichlorid zu den entsprechenden N-substituierten 2-(1-Adamantyl)-5-amino-1,3,4-thiadiazolen3a–e. Unter gleichen Reaktionsbedingungen cyclisiert das 4-Benzylthiosemicarbazid2f mit Phosphoroxytrichlorid zum 5-Benzylamino-1,3,4-thiadiazol3f, während in Schwefelsäure eine Cyclisierung unter Debenzylierung zum 5-Amino-1,3,4-thiadiazol4 erfolgt.

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Authors and Affiliations

  1. Pharmazeutisches Institut, Universität Bonn, D-53121, Bonn, Germany

    A. A. El-Emam & J. Lehmann

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  1. A. A. El-Emam
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  2. J. Lehmann
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We would like to dedicate this paper to Prof. Dr. E. Röder, Bonn, on the occasion of his 65th birthday

For part III, see Ref. [15].

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El-Emam, A.A., Lehmann, J. Adamantane derivatives IV: Unexpected debenzylation on ring closure of 1-(1-adamantylcarbonyl)-4-benzylthiosemicarbazide with sulphuric acid. Monatsh Chem 125, 587–591 (1994). https://doi.org/10.1007/BF00811852

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