Abstract
A novel and convenient one-pot synthesis of 3-amino-2H-1,2,4-triazoles from two molecules of isoselenocyanates and hydrazine hydrate via cyclodeselenisation was developed. Various 3-amino-2H-1,2,4-triazoles were obtained in moderate to good yields (33–45%, based on isoselenocyanates). The selenium powder and aromatic amine side products during the reaction could be recycled for efficient preparation of isoselenocyanates, which improved the atom economy. A plausible mechanism was proposed for the formation of the target products.
References
1.
Blank B.
,
Nichols D.M.
, and
Vaidya F.D.
, J. Med. Chem. , 1972 , 15 , 694 .
2.
Cavallaro C.L.
,
Harikrishnan L.S.
,
Chi F.
,
Dodd D.
, and
Purandare A.
, J. Comb. Chem. , 2008 , 10 , 28 .
3.
Romagnoli R.
,
Baraldi P.G.
,
Cruz-Lopez O.
,
Lopez-Cara C.
, and
Carrion M.D.
, J. Med. Chem. , 2010 , 53 , 4248 .
4.
Shi Y.J.
,
Song X.J.
,
Li X.
,
Ye T.H.
,
Xiong Y.
, and
Yu L.T.
, Chem. Pharm. Bull. , 2013 , 61 , 1099 .
5.
Singha T.
,
Singh J.
,
Naskar A.
,
Ghosh T.
,
Mondal A.
,
Kundu M.
,
Harwansh R.K.
, and
Maity T.K.
, Ind. J. Pharm. Edu. Res. , 2012 , 46 , 346 .
6.
Li X.
,
Li X.Q.
,
Liu H.M.
,
Zhou X.Z.
, and
Shao Z.H.
, Org. Med. Chem. Lett. , 2012 , 2 , 26 .
7.
Malerich J.P.
,
Lam J.S.
,
Hart B.
,
Fine R.M.
, and
Klebansky B.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 7454 .
8.
Lange J.H.M.
,
van Stuivenberg H.H.
,
Coolen H.K.A.C.
,
Adolfs T. J. P.
, and
McCreary A.C.
, J. Med. Chem. , 2005 , 48 , 1823 .
9.
Worrell B.T.
,
Malik J.A.
, and
Fokin V.V.
, Science , 2013 , 340 , 457 .
10.
Romagnoli R.
,
Baraldi P.G.
,
Salvador M.K.
, and
Prencipe F.
, J. Med. Chem. , 2014 , 57 , 6795 .
11.
Kim H.Y.
,
Kwak S.H.
,
Lee G.H.
, and
Gong Y.D.
, Tetrahedron , 2014 , 70 , 8737 .
12.
Jozsef R.
, J. Heterocylic Chem. , 1986 , 23 , 401 .
13.
Tsuge O.
,
Hatta T.
,
Tashiro H.
, and
Maeda H.
, Heterocycles , 2001 , 55 , 243 .
14.
Yin P.
,
Ma W.B.
,
Chen Y.
,
Huang W.C.
,
Deng Y.
, and
He L.
, Org. Lett. , 2009 , 11 , 5482 .
15.
Zarguil A.
,
Boukhris S.
,
Efrit M.L.
,
Souizi A.
, and
Essassi E.M.
, Tetrahedron Lett. , 2008 , 49 , 5883 .
16.
Kammoun M.
,
Chihi A.
,
Hajjem B.
, and
Bellassoued M.
, Synth. Commun. , 2008 , 38 , 148 .
17.
Gehlen H.
, Justus Liebigs Ann. Chem. , 1958 , 60 , 615 .
18.
Bibian M.
,
Martinez J.
,
Fehrentz J.A.
. Tetrahedron , 2011 , 67 , 7042 .
19.
Hu L.Y.
,
Guo J.
,
Magar S.S.
,
Fischer J.B.
,
Burke-Howie K.J.
, and
Durant G.J.
, J. Med. Chem. , 1997 , 40 , 4281 .
20.
Kaupp G.
,
Schmeyers J.
, and
Boy J.
, Chem. Eur. J. , 1998 , 4 , 2467 .
21.
Wu Y.Q.
,
Limburg D.C.
,
Wilkinson D.E.
, and
Hamilton G.S.
, Org. Lett. , 2000 , 2 , 795 .
22.
Natarajan A.
,
Guo Y.
,
Arthanari H.
,
Wagner G.
,
Halperin J.A.
, and
Chorev M.
, J. Org. Chem. , 2005 , 70 , 6362 .
23.
Guin S.
,
Rout S.K.
,
Khatun N.
,
Ghosh T.
, and
Patel B.K.
, Tetrahedron , 2012 , 68 , 5066 .
24.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Eur. J. Org. Chem. , 2005 , 3128 .
25.
Garud D.R.
,
Makimura M.
,
Ando H.
,
Ishihara H.
, and
Koketsu M.
, Tetrahedron Lett. , 2007 , 48 , 7764 .
26.
Garud D.R.
, and
Koketsu M.
, Org. Lett. , 2008 , 10 , 3319 .
27.
Garud D.R.
,
Toyoda Y.
, and
Koketsu M.
, Tetrahedron Lett. , 2009 , 50 , 3035 .
28.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Tetrahedron , 2006 , 62 , 3344 .
29.
Xie Y.Y.
,
Zhang F.
,
Li J.J.
, and
Shi X.J.
. Synlett , 2010 , 901 .