Abstract
An efficient and green protocol for the synthesis of functionalised spirooxindole derivatives is described. This involves the reaction of in situ-generated keto-enaminones with N-alkylisatins in the presence of isothiocyanates.
References
1.
Pandeya S.N.
,
Smitha S.
,
Jyoti M.
, and
Sridhar S.K.
, Acta Pharm. , 2005 , 55 , 27 .
2.
Kara L.V.
,
Julie M.L.
,
Marie R.
,
Stephen G.P.
, and
John B.B.
, J. Med. Chem. , 2007 , 50 , 5109 .
3.
Hajinasiri R.
,
Hossaini Z.
, and
Sheikholeslami-Farahani F.
, Combinat. Chem. High Throughput Screening , 2015 , 18 , 42 .
4.
Hossaini Z.
,
Soltani S.
,
Sheikholeslami-Farahani F.
,
Sayyed-Alangi S.Z.
, and
Sajjadi-Ghotabadi H.
, Chem. Heterocycl. Compd , 2015 , 51 , 26 .
5.
Hossaini Z.
,
Rostami-Charati F.
,
Ghasemian M.
, and
Afshari Sharif Abad S.
, Synlett , 2015 , 26 , 1222 .
6.
Hossaini Z.
,
Rostami-Charati F.
,
Ghambarian M.
, and
Siadati S. A.
, Phosphorus, Sulfur, Silicon Rel. Elem. , 2015 , 190 , 1177 .
7.
Slobbe P.
,
Ruijter E.
, and
Orru R.V.A.
, Med. Chem. Commun. , 2012 , 3 , 1189 .
8.
Heijden V.D.G.
,
Ruijter E.
, and
Orru R.V.A.
, Synlett , 2013 , 666 .
9.
Hulme C.
,
Ayaz M.
,
Martinez-Ariza G.
,
Medda F.
, and
Shaw A.
, in Small molecule medicinal chemistry: strategies and technologies , eds
Czechtizky W.
, and
Hamley P.
, Wiley-VCH , Weinheim , 2015 , chap. 6.
10.
Gollner A.
, Synlett , 2015 , 426 .
11.
Brown R.T.
, Indoles, the monoterpenoid indole alkaloids , Wiley , New York , 1983 , Vol. 25 .
12.
Galliford C.V.
, and
Scheidt K.A.
, Angew. Chem. Int. Ed. , 2007 , 46 , 8748 .
13.
Singh G.S.
, and
Desta Z.Y.
, Chem. Rev. , 2012 , 112 , 6104 .
14.
Santosa M.M.M.
, Tetrahedron , 2014 , 70 , 9735 .
15.
Pavlovska T.L.
,
Redkin R.Gr.
,
Lipson V.V.
, and
Atamanuk D.V.
, Mol. Divers. , 2016 , 20 , 299 .
16.
Ishikawa H.
,
Suzuki T.
, and
Hayashi Y.
, Angew. Chem. Int. Ed. , 2009 , 48 , 1304 .
17.
Ziyaei Halimehjani A.
,
Marjani K.
, and
Ashouri A.
, Green. Chem. , 2010 , 12 , 1306 .
18.
Wahba A.E.
, and
Hamann M.T.
, Mar. Drugs , 2010 , 8 , 2395 .
19.
Vaxelaire C.
,
Winter P.
, and
Christmann M.
, Angew. Chem. Int. Ed. , 2011 , 50 , 3605 .
20.
Zhao W.
, and
Chen F.E.
, Curr. Org. Synth. , 2012 , 6 , 873 .
21.
Xiang F.
,
Stuart M.
,
Vorenkamp J.
,
Roest S.
,
Timmer-Bosscha H.
,
Stuart M.C.
,
Fokkink R.
, and
Loontjens T.
, Macromolecules , 2013 , 46 , 4418 .
22.
Ali A.
,
Correa A.G.
,
Alves D.
,
Zukerman-Schpector J.
,
Westermann B.
,
Ferreira M.A.B.
, and
Paixao M.W.
, Chem. Commun. , 2014 , 11926 .
23.
Dömling A.
, and
Ugi I.
, Angew. Chem. Int. Ed. , 2000 , 9 , 3168 .
24.
Hulme C.
, and
Gore V.
, Curr. Med. Chem. , 2003 , 10 , 51 .
25.
Akritopolou-Zanze I.
, Curr. Opin. Chem. Biol. , 2008 , 12 , 324 .
26.
Dömling A.
,
Wang W.
, and
Wang K.
, Chem. Rev. , 2012 , 112 , 3083 .
27.
Dömling A.
, and
Zarganes-Tzitzikas T.
, Org. Chem. Front. , 2014 , 1 , 834 .
28.
Hossaini Z.
,
Ghambarian M.
,
Afshari Sharif Abad S.
, and
Mohtat B.
, Lett. Org. Chem. , 2015 , 12 , 176 .
29.
Sayyed Alangi S.Z.
, and
Hossaini Z.
, Chem. Heterocycl. Compd , 2015 , 51 , 541 .
30.
Li C.J.
, Chem. Rev. , 2005 , 105 , 3095 .
31.
Kobayashi S.
, and
Manabe K.
, Acc. Chem. Res. , 2002 , 35 , 209 .
32.
Lindstrom U.M.
, Chem. Rev. , 2002 , 102 , 2751 .
33.
Solhy A.
,
Elmakssoudi A.
,
Tahir R.
,
Karkouri M.
,
Larzek M.
,
Bousmina M.
, and
Zahouily M.
, Green Chem. , 2010 , 12 , 2261 .
34.
Grieco P.A.
, ed., Organic synthesis in water , Blackie Academic and Professional , London , 1998 .
35.
Anastas P.T.
, and
Warner J.C.
, Green chemistry: theory and practice , Oxford University Press , New York , 1988 .
36.
Lancester M.
, Green chemistry: an introductory text , Royal Society of Chemistry , Cambridge , 2002 .
37.
Tan J.N.
,
Li H.
, and
Gu Y.
, Green Chem. , 2010 , 12 , 1772 .
38.
Sabbaghan M.
,
Anaraki Firooz A.
, and
Jan Ahmadi V.
, J. Mol. Liq. , 2012 , 175 , 135 .
39.
Shaterian H.R.
, and
Mohammadnia M.
, J. Mol. Liq. , 2013 , 177 , 353 .
40.
Rostami-Charati F.
,
Hossaini Z.
,
Sheikholeslami-Farahani F.
,
Azizi Z.
, and
Siadati S.A.
, Combinat. Chem. High Throughput Screening , 2015 , 18 , 872 .
41.
Goerdeler J.
,
Laqua A.
, and
Lindner Ch.
, Chem. Ber. , 1974 , 107 , 3518 .
42.
Walter W.
, and
Fleck T.
, Liebigs Ann. Chem. , 1976 , 670 .
43.
Garden S.J.
,
Torres J.C.
,
da Silva L.E.
, and
Pinto A.C.
, Synth. Commun. , 1998 , 28 , 1679 .