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Über cyclische Guanidin—Mesityloxid- und Guanidin—Phoron-Kondensate

Cyclic guanidine—mesityl oxide- and guanidine—phorone condensates

Über heterocyclen, 36. Mitt.

  • Organische Chemie und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

The basic product synthesized byTraube andSchwarz from mesityl oxide and guanidine has not been 4.4.6-trimethyl-4.5-dihydro-2-pyrimidinamine (1), but a mixture containing the 4.4.6-trimethyl-3.4-dihydro-2(1H)-pyrimidinimine (resp. an isomeric pyrimidinamine)2 a (resp.2 b, 2 c) and the dimeric 4.4′-methylenedi[2(1H)-pyrimidinimine] (resp. an isomeric methylenedipyrimidinamine)3 a (resp.3 b, 2 c) and the dimerisation reaction were studied in a series of experiments. The product of the reaction of guanidine and phorone is not the guanidinopropylpyrimidine8 4, but the 4.4′-spirobi[2(1H)-pyrimidinimine] (resp. a spirobipyrimidinamine)11 a (resp.11 b, 11 c). No determination was possible on the basis of NMR whether the condensation products of guanidine—in solutions ofDMSO-d6—are pyrimidinimines (2 a, 3 a, 11 a) or pyrimidinamines (2 b resp.2 c, 3 b resp.3 c, 11 b resp.11 c) or mixtures of the isomeric compounds. The NMR-and mass spectra of2 a (resp.2 b, 2 c),3 a (resp.3 b, 3 c),11 a (resp.11 b, 11 c) and their derivates are discussed.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie der Universität Graz, Universitätsplatz 1, A-8010, Graz, Österreich

    W. Wendelin & A. Harler

Authors
  1. W. Wendelin
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  2. A. Harler
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Additional information

Herrn Prof. Dr.G. Zigeuner danken wir für die großzügige Unterstützung dieser Arbeit; den Herrn Doz. Dr.H. Sterk und Dr.G. Uray vom Institut für Organische Chemie der Universität Graz sowie Herrn Dr.A. Fuchsgruber möchten wir für die Aufnahme und Besprechung der NMR-und Massenspektren danken.

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Wendelin, W., Harler, A. Über cyclische Guanidin—Mesityloxid- und Guanidin—Phoron-Kondensate. Monatshefte für Chemie 105, 563–573 (1974). https://doi.org/10.1007/BF00912609

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  • DOI: https://doi.org/10.1007/BF00912609

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