Abstract
A simple and novel synthesis of spirocyclic oxindole derivatives by the reaction of (E)-3-arylideneindole-2-ones and 1,4-dithiane-2,5-diol via a Michael-aldol cascade under solvent-free reaction conditions is reported. This method provides a new practical and facile approach to 4′-hydroxy-2′-aryl-4’,5′-dihydro-2'H-spiro[oxindole-3,3′-thiophen]-2-ones in moderate to good yields. The structures of all the products were characterised by NMR, infrared spectroscopy and HRMS.
References
1.
Kang T.H.
,
Matsumoto K.
,
Murakami Y.
,
Takayama H.
,
Kitajima M.
,
Aimi N.
, and
Watanabe H.
, Eur. J. Pharmacol. , 2002 , 444 , 39 .
2.
Williams R.M.
, and
Cox R.J.
, Acc. Chem. Res. , 2003 , 36 , 127 .
3.
Cui C.B.
,
Kakeya H.
, and
Osada H.
., Tetrahedron , 1996 , 52 , 12651 .
4.
Sun L.
,
Liang C.
,
Shirazian S.
,
Zhou Y.
,
Miller T.
,
Cui J.
,
Fukuda J.Y.
,
Chu J.Y.
,
Nematalla A.
,
Wang X.Y.
,
Chen H.
,
Sistla A.
,
Luu T.C.
,
Tang F.
,
Wei J.
, and
Tang C.
, J. Med. Chem. , 2003 , 46 , 1116 .
5.
Mendel D.B.
,
Laird A.D.
,
Smolich B.D.
,
Blake R.A.
,
Liang C.
,
Hannah A.L.
,
Shaheen R.M.
,
Ellis L.M.
,
Weitman S.
,
Shawver L.K.
, and
Cherrington J.M.
, Anticancer Drug Des. , 2000 , 15 , 29 .
6.
Zhou L.
,
Yang J.S.
,
Wu X.
,
Zou J.H.
,
Xu X.D.
, and
Tu G.Z.
, Heterocycles , 2005 , 65 , 1409 .
7.
Robinson R.P.
,
Reiter L.A.
,
Barth W.E.
,
Campeta A.M.
,
Cooper K.
,
Cronin B.J.
,
Destito R.
,
Donahue K.M.
,
Falkner F.C.
,
Fiese E.F.
,
Johnson D.L.
,
Kuperman A.V.
,
Liston T.E.
,
Malloy D.
,
Martin J.J.
,
Mitchell D.Y.
,
Rusek F.W.
,
Shamblin S.L.
, and
Wright C.F.
, J. Med. Chem. , 1996 , 39 , 10 .
8.
Hughes C.C.
,
MacMillan J.B.
,
Gaudêncio S.P.
,
Fenical W.
, and
LaClair J.J.
, Angew. Chem. Int. Ed. , 2009 , 48 , 728 .
9.
Trost B.M.
, and
Brennan M.K.
, Synthesis , 2009 , 18 , 3003 .
10.
Orbe J.
,
Sanchez-Arias J.A.
,
Rabal O.
,
Rodriguez J.A.
,
Salicio A.
,
Ugarte A.
,
Belzunce M.
,
Xu M.
,
Wu W.
,
Tan H.
,
Ma H.
,
Paramo J.A.
, and
Oyarzabal J.
, J. Med. Chem. , 2015 , 58 , 2465 .
11.
Emami S.
, and
Ghanbarimasir Z.
, Eur. J. Med. Chem. , 2015 , 93 , 539 .
12.
Hirashima S.
,
Sakai T.
, and
Nakashima K.
, Tetrahedron Lett. , 2014 , 55 , 4334 .
13.
Xie W.L.
,
Xiao G.W.
, and
Gu L.Q.
, Chin. J. Org. Chem. , 2008 , 28 , 1123 .
14.
Pattarawarapan M.
,
Jaita S.
, and
Phakhodee W.
, Tetrahedron Lett. , 2016 , 57 , 3171 .
15.
Li X.F.
,
Zheng A.T.
,
Liu B.
,
Yu X.Y.
, and
Yi P.G.
, J. Heterocyclic Chem. , 2013 , 50 , 1198 .