Preparation of 2-Amino-4H-5,6-dihydro-1,3-selenazin-4-ones by Reaction of N,N-Unsubstituted Selenoureas with α,β-Unsaturated Acid Chlorides

Abstract

2-Dialkylamino-4H-5,6-dihydro-1,3-selenazin-4-ones were obtained by the reaction of N,N-unsubstituted selenoureas with α,β-unsaturated acid chlorides at room temperature.

heterocycles - ring closure - selenium - selenourea - 1,3-selenazine

References

<A NAME="RF08207SS-1A">1a</A> Narender M. Reddy MS. Kumar VP. Reddy VP. Nageswar YVD. Rao KR. J. Org. Chem.  2007,  72:  1849 

<A NAME="RF08207SS-1B">1b</A> Koketsu M. Sakai T. Kiyokuni T. Garud DR. Ando H. Ishihara H. Heterocycles  2006,  68:  1607 

<A NAME="RF08207SS-1C">1c</A> Koketsu M. Kogami M. Ando H. Ishihara H. Synthesis  2006,  31 

<A NAME="RF08207SS-1D">1d</A> Below H. Pfeiffer W.-D. Geisler K. Lalk M. Langer P. Eur. J. Org. Chem.  2005,  3637 

<A NAME="RF08207SS-1E">1e</A> Larsen RD. 1,3-Selenazoles, In Comprehensive Heterocyclic Chemistry II:   Vol. 3:  Katritzky AR. Rees CW. Scriven EFV. Pergamon Press; New York: 1996. 

<A NAME="RF08207SS-2A">2a</A> Sommen GL. Linden A. Heimgartner H. Helv. Chim. Acta  2007,  90:  472 

<A NAME="RF08207SS-2B">2b</A> Koketsu M. Yamamura Y. Ishihara H. Synthesis  2006,  2738 

<A NAME="RF08207SS-2C">2c</A> Koketsu M. Taura M. Ishihara H. J. Heterocycl. Chem.  2004,  41:  783 

<A NAME="RF08207SS-2D">2d</A> Fujiwara S. Shikano Y. Shin-Ike T. Kambe N. Sonoda N. J. Org. Chem.  2002,  67:  6275 

<A NAME="RF08207SS-2E">2e</A> Dubreuil D. Pradere JP. Giraudeau N. Goli M. Tonnard F. Tetrahedron Lett.  1995,  36:  237 

<A NAME="RF08207SS-2F">2f</A> Yokoyama M. Kumata K. Hatanaka H. Shiraishi T. Bull. Chem. Soc. Jpn.  1986,  59:  2909 

<A NAME="RF08207SS-3A">3a</A> Koketsu M. Takenaka Y. Ishihara H. Heteroat. Chem.  2003,  14:  106 

<A NAME="RF08207SS-3B">3b</A> Koketsu M. Takenaka Y. Hiramatsu S. Ishihara H. Heterocycles  2001,  55:  1181 

<A NAME="RF08207SS-3C">3c</A> Koketsu M. Senda T. Yoshimura K. Ishihara H. J. Chem. Soc., Perkin Trans. 1  1999,  453 

<A NAME="RF08207SS-4">4</A> Simchen G. Wenzelburger J. Chem. Ber.  1970,  103:  413 

<A NAME="RF08207SS-5A">5a</A> Gutzkow KB. Låhne HU. Naderi S. Torgersen KM. Skålhegg B. Koketsu M. Uehara Y. Blomhoff HK. Cell. Signal.  2003,  15:  871 

<A NAME="RF08207SS-5B">5b</A> Cho SI. Koketsu M. Ishihara H. Matsushita M. Nairn AC. Fukazawa H. Uehara Y. Biochim. Biophys. Acta  2000,  1475:  207 

<A NAME="RF08207SS-5C">5c</A> Wu W. Murakami K. Koketsu M. Yamada Y. Saiki I. Anticancer Res.  1999,  19:  5375 

<A NAME="RF08207SS-5D">5d</A> Koketsu M. Ishihara H. Wu W. Murakami K. Saiki I. Eur. J. Pharm. Sci.  1999,  9:  157 

<A NAME="RF08207SS-5E">5e</A> Koketsu M. Ishihara H. Hatsu M. Res. Commun. Mol. Pathol. Pharmacol.  1998,  101:  179 

<A NAME="RF08207SS-6">6</A>

Crystal structure data for 3d: Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication, CCDC No. 645675. Copies of this information can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: [phone] or e-mail: [e-mail]].

<A NAME="RF08207SS-7">7</A> Koketsu M. Ebihara M. Ishihara H. Acta Crystallogr., Sect. E  2006,  62:  o1218 

<A NAME="RF08207SS-8A">8a</A> Koketsu M. Kanoh K. Ishihara H. Heterocycles  2006,  68:  2145 

<A NAME="RF08207SS-8B">8b</A> Koketsu M. Kanoh K. Ishihara H. Heterocycles  2006,  68:  2647 

<A NAME="RF08207SS-9A">9a</A> Koketsu M. Takakura N. Ishihara H. Synth. Commun.  2002,  32:  3075 

<A NAME="RF08207SS-9B">9b</A> Koketsu M. Fukuta Y. Ishihara H. Tetrahedron Lett.  2001,  42:  6333