Regioselective synthesis of 3-nitroindoles under non-acidic and non-metallic conditions
Hua Zhang1,2, Rong-Chuan Su1,2, Yu-Li Qin1,2
1Department of Pharmacology, North Sichuan Medical College Nanchong 637100 China pzhao@nsmc.edu.cn.
Abstract:
An electrophilic substitution reaction, without acid and metal, of indole with ammonium tetramethylnitrate for accessing 3-nitroindole has been developed. In this protocol, trifluoroacetyl nitrate (CF3COONO2) was produced by metathesis of ammonium tetramethyl nitrate and trifluoroacetic anhydride at sub-room temperature. Trifluoroacetyl nitrate (CF3COONO2) is an electrophilic nitrating agent for a variety of indoles, aromatic and heterocyclic aromaticity. Meanwhile, this strategy could be applied to construct the skeleton structure of many kinds of bioactive molecules. Interestingly, 3-nitroindole can be further derivatived as a pyrrolo[2,3-b]indole.
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