Two-step route to indoles and analogues from haloarenes: a variation on the Fischer indole synthesis |
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Authors: | Inman Martyn Carbone Anna Moody Christopher J |
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Institution: | School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK. |
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Abstract: | In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines. |
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