Abstract
1,3-Selenazol-4-one derivatives were synthesized by the reaction of primary selenoamides
with haloacyl halides in the presence of pyridine.
Key words
primary selenoamide - haloacyl halide - pyridine - 1,3-selenazol-4-one - heterocycles
References
<A NAME="RF06900SS-1A">1a</A>
Katritzky AR.
Rees CW.
Scriven EFV.
Comprehensive Heterocyclic Chemistry II
Pergamon;
London:
1996.
p.1-11
<A NAME="RF06900SS-1B">1b</A>
Back TG.
Organoselenium Chemistry: A Practical Approach
Oxford University Press;
London:
1999.
<A NAME="RF06900SS-1C">1c</A>
Wirth T.
Organoselenium Chemistry: Modern Developments in Organic Synthesis
Springer;
Berlin:
2000.
<A NAME="RF06900SS-2A">2a</A>
Kumar Y.
Green R.
Borysko KZ.
Wise DS.
Wotring LL.
Townsend LB.
J. Med. Chem.
1993,
36:
3843
<A NAME="RF06900SS-2B">2b</A>
Koketsu M.
Ishihara H.
Wu W.
Murakami K.
Saiki I.
Eur. J. Pharm. Sci.
1999,
9:
157
<A NAME="RF06900SS-2C">2c</A>
Wu W.
Murakami K.
Koketsu M.
Yamada Y.
Saiki I.
Anticancer Res.
1999,
19:
5375
<A NAME="RF06900SS-2D">2d</A>
Cho SI.
Koketsu M.
Ishihara H.
Matsushita M.
Nairn AC.
Fukazawa H.
Uehara Y.
Biochim. Biophys. Acta
2000,
1475:
207
<A NAME="RF06900SS-3A">3a</A>
Cohen VI.
Synthesis
1978,
769
<A NAME="RF06900SS-3B">3b</A>
Cohen VI.
Synthesis
1979,
66
<A NAME="RF06900SS-3C">3c</A>
Shafiee A.
Mazloumi A.
Cohen VI.
J. Heterocycl. Chem.
1979,
16:
1563
<A NAME="RF06900SS-3D">3d</A>
Sekiguchi M.
Ogawa A.
Fujiwara S.
Kambe N.
Sonoda N.
Chem. Lett.
1990,
913
<A NAME="RF06900SS-3E">3e</A>
Shimada K.
Matsuda Y.
Hikage S.
Takeishi Y.
Takikawa Y.
Bull. Chem. Soc. Jpn.
1991,
64:
1037
<A NAME="RF06900SS-3F">3f</A>
Dubreuil D.
Pradère JP.
Giraudeau N.
Goli M.
Tonnard F.
Tetrahedron Lett.
1995,
36:
237
<A NAME="RF06900SS-3G">3g</A>
Koketsu M.
Senda T.
Yoshimura K.
Ishihara H.
J. Chem. Soc., Perkin Trans. 1
1999,
453
<A NAME="RF06900SS-3H">3h</A>
Koketsu M.
Hiramatsu S.
Ishihara H.
Chem. Lett.
1999,
485
<A NAME="RF06900SS-4">4</A>
Reactions of 1a and 2a at -20 °C, 0 °C, r. t. and reflux gave 3a in 69, 80, 77 and 74% yields, respectively.
<A NAME="RF06900SS-5">5</A> The reaction of thioamide with β-haloacyl halide yielded 1,3-thiazin-4-one, see:
Okawara T.
Kashimura H.
Furukawa M.
Chem. Pharm. Bull.
1985,
33:
3479
<A NAME="RF06900SS-6">6</A>
Ishihara H.
Yoshimura K.
Koketsu M.
Chem. Lett.
1998,
1287
