Abstract
A variety of biologically and synthetically useful 3-alkenyloxindoles were rapidly synthesised via an SN2′-type allylic substitution reaction of isatin-derived Morita–Baylis–Hillman carbonates with sodium sulfinates. The syntheses were conducted under catalyst-free reaction conditions and good to excellent product yields (up to 96%) and Z/E selectivities (up to >20:1) were obtained.
References
1.
Millemaggi A.
, and
Taylor R.J.K.
, Eur. J. Org. Chem. , 2010 , 4527 .
2.
Pedras M.S.C.
,
Sorensen J.L.
,
Okanga F.I.
, and
Zaharia I.L.
, Bioorg. Med. Chem. Lett. , 1999 , 9 , 3015 .
3.
Zhou L.
,
Yang J.-S.
,
Wu X.
,
Zou J.-H.
,
Xu X.-D.
, and
Tu G.-Z.
, Heterocycles , 2005 , 65 , 1409 .
4.
Tourneau C.L.
,
Raymond E.
, and
Faivre S.
, Ther. Clin. Risk Manag. , 2007 , 3 , 341 .
5.
Quintavalla A.
,
Lanza F.
,
Montroni E.
,
Lombardo M.
, and
Trombini C.
, J. Org. Chem. , 2013 , 78 , 12049 .
6.
Duan S.-W.
,
Lu H.-H.
,
Zhang F.-G.
,
Xuan J.
,
Chen J.-R.
, and
Xiao W.-J.
, Synthesis , 2011 , 1847 .
7.
Monari M.
,
Montroni E.
,
Nitti A.
,
Lombardo M.
,
Trombini C.
, and
Quintavalla A.
, Chem.-Eur. J. , 2015 , 21 , 11038 .
8.
Sun Q.-S.
,
Chen X.-Y.
,
Zhu H.
,
Lin H.
,
Sun X.-W.
, and
Lin G.-Q.
, Org. Chem. Front. , 2015 , 2 , 110 .
9.
Huang H.
,
Bihani M.
, and
Zhao J.C.-G.
, Org. Biomol. Chem. , 2016 , 14 , 1755 .
10.
Chen P.-Q.
,
Xiao Y.-C.
,
Yue C.-Z.
, and
Chen Y.-C.
, Org. Chem. Front. , 2014 , 1 , 490 .
11.
Feng J.
,
Li X.
, and
Cheng J.-P.
, Chem. Commun. , 2015 , 51 , 14342 .
12.
Chen Q.
,
Wang G.
,
Jiang X.
,
Xu Z.
,
Lin L.
, and
Wang R.
, Org. Lett. , 2014 , 16 , 1394 .
13.
Nicola D.I.
,
Paolo R.
,
Silvia R.
,
Andrea M.
,
Riccardo G.M.
, and
Giorgio B.
, J. Org. Chem. , 2015 , 80 , 7158 .
14.
Lee H.J.
,
Lee S.
,
Yu J.
, and
Kim J.N.
, Tetrahedron Lett. , 2014 , 55 , 2450 .
15.
Declerck V.
,
Martinez J.
, and
Lamaty F.
, Chem. Rev. , 2009 , 109 , 1 .
16.
Basavaiah D.
,
Reddy B.S.
, and
Badsara S.S.
, Chem. Rev. , 2010 , 110 , 5447 .
17.
Wei Y.
, and
Shi M.
, Acc. Chem. Res. , 2010 , 43 , 1005 .
18.
Liu T.-Y.
,
Xie M.
, and
Chen Y.-C.
, Chem. Soc. Rev. , 2012 , 41 , 4101 .
19.
Rios R.
, Catal. Sci. Technol. , 2012 , 2 , 267 .
20.
Wei Y.
, and
Shi M.
, Chem. Rev. , 2013 , 113 , 6659 .
21.
Xie P.
, and
Huang Y.
, Org. Biomol. Chem. , 2015 , 13 , 8578 .
22.
Zhao S.
,
Zhao Y.-Y.
,
Lin J.-B.
,
Xie T.
,
Liang Y.-M.
, and
Xu P.-F.
, Org. Lett. , 2015 , 17 , 3206 .
23.
Du F.
,
Yin L.
,
Ning Y.
, and
Peng Y.
, Adv. Synth. Catal. , 2016 , 358 , 2280 .
24.
Nishimine T.
,
Taira H.
,
Tokunaga E.
,
Shiro M.
, and
Shibata N.
, Angew. Chem., Int. Ed. , 2016 , 55 , 359 .
25.
Liu X.-W.
,
Han W.-Y.
,
Liu X.-L.
,
Zhou Y.
,
Zhang X.-M.
, and
Yuan W.-C.
, Tetrahedron , 2014 , 70 , 9191 .
26.
Peng J.
,
Huang X.
,
Cui H.-L.
, and
Chen Y.-C.
, Org. Lett. , 2010 , 12 , 4260 .
27.
Liu X.-L.
,
Jing D.-H.
,
Yao Z.
,
Zhang W.-H.
,
Liu X.-W.
,
Yang Z.-J.
,
Zhao Z.
,
Zhou Y.
, and
Li X.-N.
, Tetrahedron Lett. , 2015 , 56 , 5637 .
28.
Feng T.-T.
,
Huang X.
,
Liu X.-L.
,
Jing D.-H.
,
Liu X.-W.
,
Guo F.-M.
,
Zhou Y.
, and
Yuan W.-C.
, Org. Biomol. Chem. , 2014 , 12 , 9366 .
29.
Zhong N.-J.
,
Wei F.
,
Xuan Q.-Q.
,
Liu L.
,
Wang D.
, and
Chen Y.-J.
, Chem. Commun. , 2013 , 49 , 11071 .
30.
Vyas D.J.
,
Fröhlich R.
, and
Oestreich M.
, J. Org. Chem. , 2010 , 75 , 6720 (ESI pp. 54–56).
31.
Jacobs T.L.
,
Winstein S.
,
Linden G.B.
,
Robson J.H.
,
Levy E.F.
, and
Seymour D.
, Org. Synth. , 1948 , 28 , 70 .
32.
Selvakumar K.
,
Lingam K.A.P.
, and
Varma R.V.L.
, RSC Adv. , 2014 , 4 , 36538 .
33.
Huang X.
,
Guo F.
,
Jing D.
,
Yang J.
,
Zhou Y.
,
Liu X.
, and
Yu Z.
, Journal of Guizhou Normal University (Natural Sciences) , 2014 , 32 , 89 .
34.
Huang X.
,
Peng J.
,
Dong L.
, and
Chen Y.-C.
, Chem. Commun. , 2012 , 48 , 2439 .
35.
Liu J.-Y.
,
Lu H.
,
Li C.-G.
,
Liang Y.-M.
, and
Xu P.-F.
, Synlett , 2016 , 27 , 1287 .
36.
Zhan G.
,
Shi M.-L.
,
He Q.
,
Lin W.-J
,
Ouyang Q.
,
Du W.
, and
Chen Y.-C.
, Angew. Chem., Int. Ed. , 2016 , 55 , 2147 .