Publication: Reaction of some 4,6-dimethoxyindoles with nitric acid: Nitration and oxidative dimerisation
Issued Date
2005-01-24
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ISSN
00404020
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2-s2.0-11144298661
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Mahidol University
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SCOPUS
Bibliographic Citation
Tetrahedron. Vol.61, No.4 (2005), 853-861
Suggested Citation
Tinnagon Keawin, Shuleewan Rajviroongit, David Stc Black Reaction of some 4,6-dimethoxyindoles with nitric acid: Nitration and oxidative dimerisation. Tetrahedron. Vol.61, No.4 (2005), 853-861. doi:10.1016/j.tet.2004.11.026 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/16381
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Title
Reaction of some 4,6-dimethoxyindoles with nitric acid: Nitration and oxidative dimerisation
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Abstract
A range of 3-substituted-4,6-dimethoxyindoles bearing electron-withdrawing groups in either the 2- or 7-position, can be nitrated using nitric acid in acetonitrile, to give 7-nitro and 2-nitro-indoles, respectively. Those without electron-withdrawing groups undergo oxidative dimerisation at C7, if 2,3-disubstituted, and at C2, if N-methylated and unsubstituted at C2. Some 3-substituted-4,6-dimethoxyindoles can be nitrated using nitric acid in acetonitrile, to give 7-nitro and 2-nitro-indoles. Some undergo oxidative dimerisation at C7, if 2,3-disubstituted, and at C2, if N-methylated and unsubstituted at C2. © 2004 Elsevier Ltd. All rights reserved.