Abstract
A facile method for solid-phase organic synthesis of 1-(E)-phenylethenyl-4-substituted-1,2,3-triazoles from polystyrene-supported (2-azido-1-phenyl)ethyl selenide and substituted ethynes has been developed. The advantages of this method include straightforward operation, high yield and purity of the products, as well as lack of odour and good stability of the polymeric reagent.
Keywords
References
1.
Bannwarth W.
, In Combinatorial chemistry: a practical approach ;
Bannwarth W.
, and
Felder E.
, eds. Wiley-VCH , Weinheim , 2000 .
2.
Paulmier C.
, Selenium reagents and intermediates in organic synthesis . Pergamon Press , Oxford , 1986 .
3.
Reich H.J.
, Acc. Chem. Res. , 1979 , 12 , 22 .
4.
Nicolaou K.C.
,
Pastor J.
,
Barluenga S.
, and
Winssinger N.
, Chem. Commun. , 1998 , 1947 .
5.
Ruhland T.
,
Andersen K.
, and
Pedersen H.
, J. Org. Chem. , 1998 , 63 , 9204 .
6.
Fujita K.-I.
,
Hashimoto S.
,
Oishi A.
, and
Taguchi Y.
, Tetrahedron Lett. , 2003 , 44 , 3793 .
7.
Tang E.
,
Chen B.Z.
,
Zhang L.P.
,
Li W.
, and
Lin J.
, Synlett , 2011 , 707 .
8.
Fan W.Q.
, and
Katritzky A.R.
, In Comprehensive heterocyclic chemistry II ;
Katritzky A.R.
,
Rees C.W.
, and
Scriven E.F.V.
, eds. Elsevier , Oxford , 1996 .
9.
Krasiski A.
,
Radi Z.
,
Manetsch R.
,
Raushel J.
,
Taylor P.
,
Sharpless K.B.
, and
Kolb H.C.
, J. Am. Chem. Soc. , 2005 , 127 , 6686 .
10.
Meldal M.
, and
Tornøe C.W.
, Chem. Rev. , 2008 , 108 , 2952 .
11.
Amblard F.
,
Cho J.H.
, and
Schinazi R.F.
, Chem. Rev. , 2009 , 109 , 4207 .
12.
Kappe C.O.
, and
Van der Eycken E.
, Chem. Soc. Rev. , 2010 , 39 , 1280 .
13.
Jiang H.
,
Feng Z.
,
Wang A.
,
Liu X.
, and
Chen Z.
, Eur. J. Org. Chem. , 2010 , 1227 .
14.
Kavitha M.
,
Mahipal B.
,
Mainkar P.S.
, and
Chandrasekhar S.
, Tetrahedron Lett. , 2011 , 52 , 1658 .
15.
Tao C.-Z.
,
Cui X.
,
Li J.
,
Liu A.-X.
,
Liu L.
, and
Guo Q.-X.
, Tetrahedron Lett. , 2007 , 48 , 3525 .
16.
Xu W-M.
,
Huang X.
, and
Tang E.
, J. Comb. Chem. , 2005 , 7 , 726 .
17.
Wang Y.-G.
,
Xu W-M.
, and
Huang X.
, Synthesis , 2007 , 28 .
18.
Cao J.
, and
Huang X.
, J. Comb. Chem. , 2008 , 10 , 526 .
19.
Mao X.-C.
,
Liu X.-L.
,
Deng Q.
, and
Sheng S.-R.
, J. Chem. Res. , 2012 , 36 , 100 .
20.
Chouthaiwale P.V.
,
Karabal P.U.
,
Suryavanshi G.
, and
Sudalai A.
, Synthesis , 2010 , 3879 .
21.
Tingoli M.
,
Tiecco M.
,
Chianelli D.
,
Balducci R.
, and
Temperini A.
, J. Org. Chem. , 1991 , 56 , 6809 .
22.
Zundel G.
, Angew. Chem., Int. Ed. Engl. , 1969 , 8 , 499 .