Abstract
An efficient one-pot synthesis of 2-amino-1,3,4-selenadiazoles from isoselenocyanates, hydrazine hydrate and aromatic aldehydes has been developed. This approach provides a simple, mild and facile way to construct various derivatives in moderate to good yields (57–82%). A plausible mechanism is proposed for the formation of the target products.
References
1.
Dinesh R.G.
, and
Mamoru K.
, Molecules , 2007 , 12 , 504 .
2.
Beletskaya I.P.
, and
Ananikov V. P.
, Chem. Rev. , 2011 , 111 , 1596 .
3.
Sies H.
, Free Radical Biol. Med. , 1993 , 14 , 313 .
4.
Schewe T.
, Gen. Pharmac. , 1995 , 26 , 1153 .
5.
Mlochowski J.
, Phosphorus, Sulfur Silicon Relat. Elem. , 1998 , 136 , 191 .
6.
Garcia S.
, Curr. Med. Chem. , 2004 , 11 , 1657 .
7.
Dogan H.N.
,
Duran A.
,
Rollas S.
,
Sener G.
,
Uysalb M. K.
, and
Gulenc D.
, Bioorg. Med. Chem. , 2002 , 10 , 2893 .
8.
Chou J.-Y.
,
Lai S.-Y.
,
Pan S.-L.
,
Jow G.-M.
,
Chern J.-W.
, and
Guh J. H.
, Biochem. Pharmacol. (Amsterdam, Netherlands) , 2003 , 66 , 115 .
9.
Sato M.
,
Kamita T.
,
Nakadera K.
, and
Mukaida K.-I.
, Eur. Polym. J. , 1995 , 31 , 395 .
10.
Bentiss F.
,
Lagrenee M.
,
Wignacourt J. P.
, and
Holt E. M.
, Polyhedron , 2002 , 21 , 403 .
11.
Wilton-Ely J.D.
,
Schier A.
, and
Schmidbaur H.
, Organometallics , 2001 , 20 , 1895 .
12.
Sybo B.
,
Bradley P.
,
Grubb A.
,
Miller S.
,
Proctor K. J.
,
Clowes L.
,
Lawrie M. R.
,
Sampson P.
, and
Seed A. J.
, J. Mater. Chem. , 2007 , 17 , 3406 .
13.
Stolle R.
, and
Gutmann L.
, J. Prakt. Chem. , 1904 , 69 , 509 .
14.
Kendall R.V.
, and
Olofson R. A.
, J. Org. Chem. , 1970 , 35 , 806 .
15.
Bolka E.
,
Ehlers D.
, and
Storm H.
J. Prakt. Chem. , 1973 , 315 , 164 .
16.
Bolka E.
, and
Ehlers D.
, J. Prakt. Chem. , 1973 , 315 , 155 .
17.
Cohen I.V.
, J. Heterocycl. Chem. , 1979 , 16 , 806 .
18.
Hua G.
,
Li Y.
,
Fuller A. L.
,
Slawin A. M. Z.
, and
Woollins J. D.
, Eur. J. Org. Chem. , 2009 , 2009 , 1612 .
19.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Eur. J. Org. Chem. , 2005 , 2005 , 3128 .
20.
Garud D.R.
,
Makimura M.
,
Ando H.
,
Ishihara H.
, and
Koketsu M.
, Tetrahedron Lett. , 2007 , 48 , 7764 .
21.
Garud D.R.
, and
Koketsu M.
, Org. Lett. , 2008 , 10 , 3319 .
22.
Garud D.R.
,
Toyoda Y.
, and
Koketsu M.
, Tetrahedron Lett. , 2009 , 50 , 3035 .
23.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Tetrahedron , 2006 , 62 , 3344 .
24.
Fernández-Bolaños J.G.
,
López Ó.
,
Ulgar V.
,
Maya I.
, and
Fuentes J.
, Tetrahedron Lett. , 2004 , 45 , 4081 .
25.
López Ó.
,
Maza S.
, and
Ulgar V.
, Tetrahedron , 2009 , 65 , 2556 .