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A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes

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Abstract

2,4-Dinitrotoluene reacts in the presence of catalytic amounts of DBU with aldehydes to form the corresponding alcohols in good yields (usually above 65%). The obtained alcohols can be readily oxidized to 2,4-dinitrobenzyl ketones, which were used for the synthesis of 6-nitroindoles with various substituents in the 2-position. Starting from non-racemic aldehydes, non-racemic 2-substituted 6-nitroindoles were obtained.

Graphical abstract: A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes

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Publication details

The article was received on 12 Dec 2017, accepted on 16 Jan 2018 and first published on 17 Jan 2018


Article type: Paper
DOI: 10.1039/C7NJ04919F
Citation: New J. Chem., 2018, Advance Article
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    A general and convenient method for the synthesis of 2,4-dinitrobenzyl ketones. Almost unlimited access to 2-substituted 6-nitroindoles from 2,4-dinitrotoluene and aldehydes

    R. Bujok, M. Wiszniewski, P. Cmoch and Z. Wróbel, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ04919F

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