Transformation of O-Amidinylhydroxylamine into Benzothiazoles via Iminocarbonyl Sulfenamides

• Autorzy: Sączewski, F.. , Kornicka, A. , Gdaniec, M.
• Języki publikacji: EN

Abstrakty

EN

The reaction of O-amidinylhydroxylamine 3 with aryl isothiocyanates leads to the formation of benzothiazole derivatives 5a-c. The proposed mechanism of the reaction involves initial formation of iminocarbonyl sulfenamides A which, in turn, undergo spontaneous sulfurization of aromatic ring with loss of amine 7. The later compound reacts with excess aryl isothiocyanate to give ,3-diazaspiro[4,5]decane-2-thione 6.

Słowa kluczowe

EN

O-amidinylhydroxylamine; (benzothiazol-2-yl)imidazolidin-2-ones; 1,3-diazaspiro[4,5]decane-2-thione; X-ray crystallography; synthesis

• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 1
• Strony: 115-120
• Opis fizyczny: Bibliogr. 12 poz., rys.

Twórcy

autor

Sączewski, F..

• Department of Chemical Technology of Drugs, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland

autor

Kornicka, A.

• Department of Chemical Technology of Drugs, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416 Gdańsk, Poland

autor

Gdaniec, M.

• Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznañ, Poland

Bibliografia

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• 5. Sączewski F., Kornicka A., Gdaniec M., Halasa R. and Werel W., Eur. J. Org. Chem., 5311 (2004).
• 6. The geometries of A, 6: and 6b have been optimized by ab initio method at the 6-3 1 G*** level using the Spartan v. 5.0 program, Wavefunction, Inc., Irvine, CA 92715, 1998, installed on a Silicon Graphics 02 workstation. Atomic charges and total energies were calculated at the same level.
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• 12. CCDC 251805 (compound 5a) and CCDC 251806 (compound 6) contain the supplementary crystallo-graphic data for these compounds. The data can be obtained free of charge via www.cedc.cam.ac.uklconts/retrieving.html (or fiom the Cambridge Crystallographic Data Centre,
• 12, Union Road, Cambridge CB2 IEZ, UK; fax: [phone]; or [e-mail]).