Abstract
The treatment of substituted acryloyl isoselenocyanates with sodium hydroselenide gave 2-selenoxoperhydro-1,3-selenazin-4-ones. The reaction of diselenocarbamates, generated from alkyl isoselenocyanates and sodium hydroselenide, with bromoacetyl bromide afforded 2-selenoxo-1,3-selenazolidin-4-ones.
Key words
isoselenocyanate - diselenocarbamate - selenazine - selenazole - sodium hydroselenide
References
1a
Comprehensive Heterocyclic Chemistry II
Vols. 1-11:
Katritzky AR.
Rees CW.
Scriven EFV.
Pergamon;
Oxford:
1996.
1b
Back TG.
Organoselenium Chemistry: A Practical Approach
Oxford University Press;
Oxford:
1999.
1c
Organoselenium Chemistry. Modern Developments in Organic Synthesis, In Topics in Current Chemistry
Vol. 208:
Wirth T.
Springer;
Heidelberg:
2000.
1d
Murai T.
Kato S.
Top. Curr. Chem.
2000,
208:
177
1e
Ishihara H.
Koketsu M.
Fukuta Y.
Nada F.
J. Am. Chem. Soc.
2001,
123:
8408
2a
Koketsu M.
Ishihara H.
Wu W.
Murakami K.
Saiki I.
Eur. J. Pharm. Sci.
1999,
9:
157
2b
Wu W.
Murakami K.
Koketsu M.
Yamada Y.
Saiki I.
Anticancer Res.
1999,
19:
5375
2c
Cho SI.
Koketsu M.
Ishihara H.
Matsushita M.
Nairn AC.
Fukazawa H.
Uehara Y.
Biochim. Biophys. Acta
2000,
1475:
207
2d
Koketsu M.
Choi SY.
Ishihara H.
Lim BO.
Kim H.
Kim SY.
Chem. Pharm. Bull.
2002,
50:
1594
2e
Gutzkow KB.
Låhne HU.
Naderi S.
Torgersen KM.
Skålhegg B.
Koketsu M.
Uehara Y.
Blomhoff HK.
Cell. Signal.
2003,
15:
871
3
Park Y.-J.
Koketsu M.
Kim JM.
Yeo J.-H.
Ishihara H.
Lee K.-G.
Kim SY.
Kim C.-K.
Biol. Pharm. Bull.
2003,
26:
1657
4a
Koketsu M.
Takenaka Y.
Ishihara H.
Synthesis
2001,
731
4b
Zhang P.-F.
Chen Z.-C.
Synthesis
2000,
1219
4c
Koketsu M.
Senda T.
Yoshimura K.
Ishihara H.
J. Chem. Soc., Perkin Trans. 1
1999,
453
4d
Lai LL.
Reid DH.
Synthesis
1993,
870
4e
Moriarty RM.
Vaid BK.
Duncan MP.
Levy SG.
Prakash O.
Goyal S.
Synthesis
1992,
845
4f
Shimada K.
Matsuda Y.
Hikage S.
Takeishi Y.
Takikawa Y.
Bull. Chem. Soc. Jpn.
1991,
64:
1037
4g
Shafiee A.
Shafaati A.
Habibi-Khameneh B.
J. Heterocycl. Chem.
1989,
26:
709
4h
Cohen VI.
Synthesis
1979,
66
4i
Potts KT.
Huang F.
Khattak RK.
J. Org. Chem.
1977,
42:
1644
4j
Cava MP.
Saris LE.
J. Chem. Soc., Chem. Commun.
1975,
617
5a
Sommen GL.
Linden A.
Heimgartner H.
Eur. J. Org. Chem.
2005,
3128
5b
Atanassov PK.
Linden A.
Heimgartner H.
Helv. Chim. Acta
2004,
87:
1452
5c
Atanassov PK.
Linden A.
Heimgartner H.
Helv. Chim. Acta
2003,
86:
3235
5d
Billert T.
Beckert R.
Doring M.
Gorls H.
J. Prakt. Chem.
1999,
341:
332
5e
Banert K.
Toth C.
Angew. Chem., Int. Ed. Engl.
1995,
34:
1627
6a
Sommen GL.
Linden A.
Heimgartner H.
Heterocycles
2005,
65:
1903
6b
Zhou Y.
Heimgartner H.
Helv. Chim. Acta
2000,
83:
539
6c
Kanda T.
Aoki H.
Mizoguchi K.
Shiraishi S.
Murai T.
Kato S.
Organometallics
1996,
15:
5753
7a
Koketsu M.
Fukuta Y.
Ishihara H.
J. Org. Chem.
2002,
67:
1008
7b
Koketsu M.
Ishida M.
Takakura N.
Ishihara H.
J. Org. Chem.
2002,
67:
486
7c
Koketsu M.
Nada F.
Hiramatsu S.
Ishihara H.
J. Chem. Soc., Perkin Trans. 1
2002,
737
7d
Koketsu M.
Fukuta Y.
Ishihara H.
Tetrahedron Lett.
2001,
42:
6333
7e
Ishihara H.
Koketsu M.
Fukuta Y.
Nada F.
J. Am. Chem. Soc.
2001,
123:
8408
8a
Thompson DP.
Boudjouk P.
J. Org. Chem.
1988,
53:
2109
8b
Klayman DL.
Griffin TS.
J. Am. Chem. Soc.
1973,
95:
197
8c
Gladysz JA.
Hornby JL.
Garbe JE.
J. Org. Chem.
1978,
43:
1204
9 This structure is novel. There is only one example of preparation of pyrido[3,2-e ]-1,3-selenazine and pyrido[3,4-e ]-1,3-selenazine ring compounds, see: Kristian P.
Koscik D.
Gonda J.
Collect. Czech. Chem. Commun.
1983,
48:
3567
Two patents regarding 2-thioxo-1,3-selenazolidin-4-one have appeared see, (a) and (b), while (b) also reports 2-selenoxo-1,3-selenazolidin-4-ones:
10a Suga T, Mine K, Takahashi Y, and Fujimori N. inventors; JP 50071325.
; Chem. Abstr. 1976 , 52086
10b Sieglitz A, and Heimke P. inventors; DE 700555.
11 CCDC 298139 for 4a contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033.
12a
Casar Z.
Leban I.
Majcen-Le Marechal A.
Lorcy D.
J. Chem. Soc., Perkin Trans. 1
2002,
1568
12b
Koketsu M.
Nada F.
Ishihara H.
Synthesis
2002,
195
12c
Brown GA.
Anderson KMM.
Murray KM.
Gallagher T.
Hales NJ.
Tetrahedron
2000,
56:
5579
12d
Cruz A.
Macias-Mendoza D.
Barragan-Rodriguez E.
Tlahuext H.
Noth H.
Contreras R.
Tetrahedron: Asymmetry
1997,
8:
3903