Abstract
A cross-coupling reaction of diaryl disulfides with substituted 5-chloropyrazole-4-aldehydes has been developed using 10 mol% of copper powder as the catalyst and caesium carbonate as the base, in DMSO at 90°C for 5–15 h under an atmosphere of nitrogen to give a series of new functionalised pyrazole sulfides in good to excellent yields (71–94%).
References
1.
Kondo T.
, and
Mitsudo T.
, Chem. Rev. , 2000 , 100 , 3205 .
2.
Hassan J.
,
Sevignon M.
,
Gozzi C.
,
Schulz E.
, and
Lemaire M.
, Chem. Rev. , 2002 , 102 , 1359 .
3.
Thomas A.W.
, and
Ley S.V.
, Angew. Chem. Int. Ed. , 2003 , 42 , 5400 .
4.
Fukuzawa S.
,
Tanihara D.
, and
Kikuchi S.
, Synlett. , 2006 , 13 , 2145 .
5.
Jammi S.
,
Barua P.
,
Rout L.
,
Saha P.
, and
Punniyamurthy T.
, Tetrahedron Lett. , 2008 , 49 , 1484 .
6.
Xu H.
,
Zhao X.
,
Deng J.
,
Fu Y.
, and
Feng Y.
, Tetrahedron Lett. , 2009 , 50 , 434 .
7.
Buchwald S.L.
, and
Bolm C.
, Angew. Chem. Int. Ed. , 2009 , 48 , 5586 .
8.
Chowdhury S.
, and
Roy S.
, Tetrahedron Lett. , 1997 , 38 , 2149 .
9.
Peppe C.
, and
Borges deCastro L.
, Can. J. Chem. , 2009 , 87 , 678 .
10.
Kumar S.
, and
Engman L.
, J. Org. Chem. , 2006 , 71 , 5400 .
11.
Feng Y.
,
Wang H.F.
,
Sun F.F.
,
Li Y.M.
,
Fu X.M.
, and
Jin K.
, Tetrahedron , 2009 , 65 , 9737 .
12.
Pantaleón O.B.
,
Ortega S.H.
, and
Morales D.M.
, Adv. Synth. Catal. , 2006 , 348 , 236 .
13.
Taniguchi N.
, J. Org. Chem. , 2004 , 69 , 6904 .
14.
Taniguchi N.
, and
Onami T.
, J. Org. Chem. , 2004 , 69 , 915 .
15.
Boyne M.
,
Stratton C.
,
Johnson F.
, and
Tonge P.
, ACS Chem. Biol. , 2006 , 1 , 43 .
16.
Vicentini C.B.
,
Guccione S.
,
Giurato L.
,
Ciaccio R.
,
Mares D.
, and
Forlani G.
, J. Agric. Food. Chem. , 2005 , 53 , 3848 .
17.
Baraldi P.G.
,
Balboni G.
,
Pavani M.G.
,
Spalluto G.
,
Tabrizi M.A.
,
Clercq E.D.
,
Balzarini J.
,
Bando T.
,
Sugiyama H.
, and
Romagnoli R.
, J. Med. Chem. , 2001 , 44 , 2536 .
18.
Goel A.
, and
Madan A.K.
, J. Chem. Inf. Comput. Sci. , 1995 , 35 , 510 .
19.
Park M.S.
,
Park H.J.
,
Park K.H.
, and
Lee K.I.
, Synth. Commun. , 2004 , 34 , 1541 .
20.
Wang H.F.
,
Jiang L.L.
,
Chen T.
, and
Li Y.M.
, Eur. J. Org. Chem. , 2010 , 2324 .
21.
Yang L.M.
,
Hua S.B.
, and
Liu Z.J.
, Chin. J. Appl. Chem. , 2005 , 22 , 829 .
