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Über die Reaktionen von Guanidin bzw. Thioharnstoff mit α,β,γ,δ-ungesättigten Ketonen

Reactions of guanidine and thiourea with α,β,γ,δ-unsaturated ketones (heterocyclic compounds, 80)

Über Heterocyclen, 80. Mitteilung

  • Organische Chemie Und Biochemie
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Abstract

Guanidine and phenylguanidine react with phenylhexadienone1b and 1,5-diaryl-2,4-pentadien-1-ones1c–k respectively (via unstable dihydropyrimidines of type2 as intermediates) to 4-methyl- and 4-aryl-6-styryl-2-pyrimidinamines3b–j and N2-phenyl-2-pyrimidinamines7c, k. Efforts to stabilize the intermediates2 by introduction of electron-withdrawing substituents (compare2,3) were not successful. Similarly, thiourea reacts with diphenylpentadienone1c to afford (via8c) 4-phenyl-6-phenethylpyrimidinethione9c.

Action of guanidine on 1,3,5-triphenylpentadienone101 and on the 5-(3-chlorophenyl) analogue10m under decomposition of the ketones yields 4,6-diphenyl-and 4-(3-chlorophenyl)-6-phenyl-2-pyrimidineamine (121 andm), respectively. The formation of12m proves that acetophenone splits off from101,m during the reactions. However, heating of thiourea with10m in sodium butylate/butanol gives the expected 4,6-diphenyl-4-styryldihydropyrimidinethione13m.

The reaction of thiourea with triphenylpentadienone101 is taking an atypical course: Addition of thiourea to the δ- and β-carbon atom of101 affords 2-(4,6-diphenyl-2-thioxohexahydro-4-pyrimidinyl)acetophenone (141); the conformation of the latter was deduced from1H-NMR data.

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Authors and Affiliations

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

    Winfried Wendelin, Hans-Wolfgang Schramm & Andreas Blasi-Rabassa

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  1. Winfried Wendelin
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  2. Hans-Wolfgang Schramm
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  3. Andreas Blasi-Rabassa
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Herrn Prof. Dr.Josef Schurz mit den besten Wünschen zum 65. Geburtstag gewidmet.

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Wendelin, W., Schramm, HW. & Blasi-Rabassa, A. Über die Reaktionen von Guanidin bzw. Thioharnstoff mit α,β,γ,δ-ungesättigten Ketonen. Monatsh Chem 116, 385–400 (1985). https://doi.org/10.1007/BF00799973

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