Abstract
Chlorination of 2-aryl-1-hydroxyindole-5,6-dicarbonitriles with N-chlorosuccinimide affords previously unknown 3,3-dichloro-3H-indole 1-oxides instead of the expected 1-hydroxy- 3-chloroindoles. The latter can be prepared in good yields by treatment of the above 3,3-dichloro-3H-indole 1-oxides with piperidine in ethanol.
References
1.
Chirkova Z.V., Kabanova M.V., Filimonov S.I., Abramov I.G., Petzer A., Petzer J.P., Suponitsky K.Y.
Bioorganic and Medicinal Chemistry Letters,
2016
2.
Chirkova Z.V., Kabanova M.V., Filimonov S.I., Abramov I.G., Petzer A., Petzer J.P., Firgang S.I., Suponitsky K.Y.
Bioorganic and Medicinal Chemistry Letters,
2015
3.
Molecular engineering of organic sensitizers containing indole moiety for dye-sensitized solar cells
Kim D., Kang M., Song K., Kang S.O., Ko J.
Tetrahedron,
2008
4.
Anbarasan P., Schareina T., Beller M.
Chemical Society Reviews,
2011
5.
6.
Jiang X., Yang J., Zhang F., Yu P., Yi P., Sun Y., Wang Y.
Advanced Synthesis and Catalysis,
2016
7.
Erickson K.L., Brennan M.R., Namnum P.A.
Synthetic Communications,
1981
8.
Silveira C.C., Mendes S.R., Wolf L., Martins G.M., von Mühlen L.
Tetrahedron,
2012
9.
Guney T., Lee J.J., Kraus G.A.
Organic Letters,
2014
10.
Samanta R.C., Yamamoto H.
Chemistry - A European Journal,
2015
11.
Thongsornkleeb C., Maibunkaew T., Tummatorn J., Bunrit A., Ruchirawat S.
Synlett,
2014
12.
Gabriel S., Gerhard W., Wolter R.
Berichte der deutschen chemischen Gesellschaft (A and B Series),
1923
13.
NAGAYOSHI T., SAEKI S., HAMANA M.
Chemical and Pharmaceutical Bulletin,
2011
14.
10.1016/j.mencom.2017.09.023_sbref0040c
Görlitzer
Pharmazie,
1998
15.
NAGAYOSHI T., SAEKI S., HAMANA M.
Chemical and Pharmaceutical Bulletin,
2011
16.
Slätt J., Bergman J.
Tetrahedron,
2002
17.
Marfat A., Carta M.P.
Tetrahedron Letters,
1987
18.
Shchekotikhin A.E., Luzikov Y.N., Sinkevich Y.B., Buyanov V.N., Preobrazhenskaya M.N.
Chemistry of Heterocyclic Compounds,
2008
19.
Filimonov S.I., Chirkova Z.V., Sharunov V.S., Abramov I.G., Stashina G.A., Firgang S.I., Suponitsky K.Y.
Chemistry of Heterocyclic Compounds,
2012
20.
Chirkova Z.V., Kabanova M.V., Sergeev S.S., Filimonov S.I., Abramov I.G., Samet A.V., Suponitsky K.Y.
Mendeleev Communications,
2015