Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence |
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| Authors: | Alexander V. Aksenov Dmitrii A. Aksenov Nicolai A. Aksenov Anton A. Skomorokhov Elena V. Aleksandrova Michael Rubin |
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| Affiliation: | Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009 Russian Federation.; Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence KS 66045-7582 USA, Fax: +1-785-864-5396, +1-785-864-5071 |
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| Abstract: | A highly efficient one-pot procedure combining conjugate addition of Grignard reagents to (2-nitroalkenyl)indoles and sub-sequent Brønsted acid-assisted spirocyclization allowed for preparation of 4′H-spiro[indole-3,5′-isoxazoles] in a diastereomerically selective fashion. Utilization of alkyl Grignard reagents provided an easy access to 4′-alkylsubstituted derivatives hardly available by other means.One-pot procedure combining conjugate addition of Grignard reagents to (2-nitroalkenyl)indoles and subsequent acid-assisted spirocyclization allowed for diastereoselective preparation of 4′H-spiro[indole-3,5′-isoxazoles]. |
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