Abstract
An efficient and metal-free method was developed to synthesise 3-sulfenylindoles via the iodine-mediated electrophilic cyclisation of 2-alkynylanilines with disulfides. In the presence of I2, various 3-sulfenylindoles were obtained in moderate to high yields.
References
1.
Weng J.R.
,
Tsai C.H.
,
Kulp S.K.
, and
Chen C.S.
, Cancer Lett. , 2008 , 262 , 153 .
2.
Rieck G.C.
, and
Fiander A.N.
, Mol. Nutr. Food Res. , 2008 , 52 , 105 .
3.
Brancale A.
, and
Silvestri R.
, Med. Res. Rev. , 2007 , 27 , 209 .
4.
La. Regina G.
,
Edler M.C.
,
Brancale A.
,
Kandil S.
,
Coluccia A.
,
Piscitelli F.
,
Hamel E.
,
De Martino G.
,
Matesanz R.
,
Díaz J.F.
,
Scovassi A.I.
,
Prosperi E.
,
Lavecchia A.
,
Novellino E.
,
Artico M.
, and
Silvestri R.
, J. Med. Chem. , 2007 , 50 , 2865 .
5.
Zhao Z.
,
Wolkenberg S.E.
,
Lu M.
,
Munshi V.
,
Moyer G.
,
Feng M.
,
Carella A.V.
,
Ecto L.T.
,
Gabryelski L.J.
,
Lai M.T.
,
Prasad S.G.
,
Yan Y.
,
McGaughey G.B.
,
Miller M.D.
,
Lindsley C.W.
,
Hartman G.D.
,
Vacca J.P.
, and
Williams T.M.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 554 .
6.
Roy K.
, and
Mandal A.S.
, J. Enzyme Inhib. Med. Chem. , 2008 , 23 , 980 .
7.
Campbell J.A.
,
Broka C.A.
,
Gong L.
,
Walker K.A.
, and
Wang J.H.
, Tetrahedron Lett. , 2004 , 45 , 4073 .
8.
Yadav J.S.
,
Reddy B.V.S.
, and
Reddy Y.J.
, Tetrahedron Lett. , 2007 , 48 , 7034 .
9.
Wu G.
,
Wu J.
,
Wu J.
, and
Wu L.
, Synth. Commun. , 2008 , 38 , 1036 .
10.
Tudge M.
,
Tamiya M.
,
Savarin C.
, and
Humphrey G.R.
, Org. Lett. , 2006 , 8 , 565 .
11.
Shirani H.
,
Stensland B.
,
Bergman J.
, and
Janosik T.
, Synlett. , 2006 , 2459 .
12.
Shirani H.
, and
Janosik T.
, Synthesis , 2007 , 2690 .
13.
Barraja P.
,
Diana P.
,
Carbone A.
, and
Cirrincione G.
, Tetrahedron , 2008 , 64 , 11625 .
14.
Chen Y.
,
Cho C.H.
, and
Larock R.C.
, Org. Lett. , 2009 , 11 , 173 .
15.
Du H.A.
,
Tang R.Y.
,
Deng C.L.
,
Liu Y.
,
Li J.H.
, and
Zhang X.G.
, Adv. Syn. Catal. , 2011 , 353 , 2739 .
16.
Du H.A.
,
Zhang X.G.
,
Tang R.Y.
, and
Li J.H.
, J. Org. Chem. , 2009 , 74 , 7844 .
17.
Chen Y.
,
Cho C.H.
,
Shi F.
, and
Larock R.C.
, J. Org. Chem. , 2009 , 74 , 6802 .
18.
Li Z.
,
Hong L.
,
Liu R.
,
Shen J.
, and
Zhou X.
, Tetrahedron Lett. , 2011 , 52 , 1343 .
19.
Guo Y.J.
,
Tang R.Y.
,
Li J.H.
,
Zhong P.
, and
Zhang X.G.
, Adv. Synth. Catal. , 2009 , 351 , 2615 .
20.
Atkinson J.G.
,
Hamel P.
, and
Girard Y.
, Synthesis , 1988 , 480 .
21.
Kraus G.A.
,
Guo H.
,
Kumar G.
,
Pollock G.
,
Carruthers H.
,
Chaudhary D.
, and
Beasley J.
, Synthesis , 2010 , 1386 .