Abstract
A one-pot reaction of arylisoselenocyanates, hydrazine and bis(trichloromethyl) carbonate, in the presence of a base provides an efficient route for the synthesis of 5-arylamino-1,3,4-selenadiazol-2(3H)-ones in good to excellent yields. A plausible mechanism is proposed for the reaction.
References
1.
Wilson S.R.
,
Zucker P.A.
, and
Huang R.R.
, J. Am. Chem. Soc. , 1989 , 111 , 5936 .
2.
Messali M.
,
Christiaents L.E.
,
Alshahateet S.F.
, and
Kooli F.
, Tetrahedron Lett. , 2007 , 48 , 7448 .
3.
Swearingen J.W. Jr
,
Fuentes D.E.
,
Araya M.A.
,
Pflishker M.F.
,
Saavedra C.P.
,
Chasteen T.G.
, and
Vasquez C.C.
, Appl. Env. Microbiol. , 2006 , 72 , 963 .
4.
Petragnani N.
,
Stefani A.
, and
Valduga C.J.
, Tetrahedron , 2001 , 57 , 1411 .
5.
Nicolaou K.C.
,
Fylaktakidou K.C.
,
Mitchell H.J.
,
Van Delft F.L.
,
Conlen S.R.
, and
Jin Z.
, Chem. Eur. J. , 2000 , 6 , 3166 .
6.
Koketsu M.
,
Yang H.O.
,
Kim Y.M.
,
Ichihashi M.
, and
Ishihara H.
, Org. Lett. , 2001 , 3 , 1705 .
7.
Johnston B.D.
,
Ghavami A.
,
Jensen M.T.
,
Svensson B.
, and
Pinto B.M.
, J. Am. Chem. Soc. , 2002 , 124 , 8245 .
8.
Sharma A.K.
,
Sharma A.
,
Desai D.
, and
Madhunapantula S.V.
, J. Med. Chem. , 2008 , 51 , 7820 .
9.
Terazawa R.
,
Garud D.R.
,
Hamada N.
,
Fujita Y.
, and
Itoh T.
, Bioorg. Med. Chem. , 2010 , 18 , 7001 .
10.
Zhang J.H.
, and
Cheng Y.
, Org. Biomol. Chem. , 2009 , 7 , 3264 .
11.
Ibañez E.
,
Plano D.
,
Font M.
,
Calvo C.
,
Prior C.
, and
Palop J.A.
, Eur. J. Med. Chem. , 2011 , 46 , 265 .
12.
Abdel-Hafez S.H.
, Eur. J. Med. Chem. , 2008 , 43 , 1971 .
13.
Scholz M.
,
Ulbrich H.K.
, and
Dannhardt G.
, Eur. J. Med. Chem. , 2008 , 43 , 1152 .
14.
Karnik A.V.
,
Kulkarni A.M.
,
Malviya N.J.
,
Mourya B.R.
, and
Jadhav B.L.
, Eur. J. Med. Chem. , 2008 , 43 , 2615 .
15.
Sivapriya K.
,
Suguna P.
,
Banerjee A.
,
Saravanan V.
,
Rao D.N.
, and
Chandrasekaran S.
, Bioorg. Med. Chem. , 2007 , 17 , 6387 .
16.
Plano D.
,
Baquedano Y.
,
Moreno-Mateos D.
, and
Font M.
, Eur. J. Med. Chem. , 2011 , 46 , 3315 .
17.
Ueda S.
,
Terauchi H.
,
Suzuki K.
,
Yano A.
,
Matsumoto M.
, and
Kubo T.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 1361 .
18.
Kumar S.
,
Johansson H.
,
Engman L.
,
Valgimigli L.
,
Amorati R.
,
Fumo M.G.
, and
Pedulli G.F.
, J. Org. Chem. , 2007 , 72 , 2583 .
19.
Hossain S.U.
,
Sengupta S.
, and
Bhattacharya S.
, Bioorg. Med. Chem. , 2005 , 13 , 5750 .
20.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Helv. Chim. Acta , 2007 , 90 , 1849 .
21.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Eur. J. Org. Chem. , 2005 , 14 , 3128 .
22.
Atanassov P.K.
,
Linden A.
, and
Heimgartner H.
, Helv. Chim. Acta , 2004 , 87 , 1873 .
23.
Atanassov P.K.
,
Linden A.
, and
Heimgartner H.
, Helv. Chim. Acta , 2003 , 86 , 3235 .
24.
Zhou Y.H.
,
Linden A.
, and
Heimgartner H.
, Helv. Chim. Acta , 2000 , 83 , 1576 .
25.
Atanassov P.K.
,
Zhou Y.H.
,
Linden A.
, and
Heimgartner H.
, Helv. Chim. Acta , 2002 , 85 , 1102 .
26.
López Ó.
,
Maza S.
,
Ulgar V.
,
Maya I.
, and
Fernández-Bolaños J.G.
, Tetrahedron , 2009 , 65 , 2556 .
27.
Fernández-Bolaños J.G.
,
López Ó.
,
Ulgar V.
,
Maya I.
, and
Fuentes J.
, Tetrahedron Lett. , 2004 , 45 , 4081 .
28.
Su W.K.
, and
Jin C.
, Org. Lett. , 2007 , 9 , 993 .
29.
Su W.K.
,
Zhang Y.
,
Li J.J.
, and
Li P.
, Org. Prep. Proced. Int. , 2008 , 40 , 543 .
30.
Li Z.H.
,
Zheng C.
, and
Su W.K.
, J. Heterocyclic Chem. , 2008 , 45 , 1195 .
31.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Tetrahedron , 2006 , 62 , 3344 .
32.
Sivapriya K.
,
Suguna P.
,
Banerjee A.
,
Saravanan V.
,
Rao D.N.
, and
Chandrasekaran S.
, Bioorg. Med. Chem. , 2007 , 17 , 6387 .
33.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Lett. Org. Chem. , 2007 , 4 , 7 .
34.
Bulka E.
,
Ehlers D.
,
Storm H.
, and
Sekt C.
, J. Prakt. Chemie , 1973 , 315 , 164 .
35.
Hua G.X.
,
Li Y.
,
Fuller Y.A.L.
,
Slawin M.Z.
, and
Woollins J.D.
, Eur. J. Org. Chem. , 2009 , 161 , 1612 .
36.
Dahman Andaloussi M.B.
, and
Mohr F.
, J. Org. Chem. , 2010 , 695 , 1276 .