One-pot synthesis of 1,4-dihydro-3,1-benzoxazine-2-thiones by the reaction of 2-lithiophenyl isothiocyanates with aldehydes or ketones |
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| Authors: | Kazuhiro Kobayashi Yuki Yokoi Toshihide Komatsu Hisatoshi Konishi |
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| Institution: | Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan |
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| Abstract: | An efficient one-pot method for the synthesis of 4-monosubstituted and 4,4-disubstituted 1,4-dihydro-3,1-benzoxazine-2-thiones has been developed. Treatment of 2-bromophenyl isothiocyantes with butyllithium in THF at −78 °C generates 2-lithiophenyl isothiocyanates, which are allowed to react with various carbonyl compounds, including aldehydes, ketones, and butanolide, to give the corresponding desired products in moderate to good yields. |
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| Keywords: | 1 4-Dihydro-3 1-benzoxazine-2-thiones 2-Lithiophenyl isothiocyanates Bromine-lithium exchange Nucleophilic addition Cyclization reaction |
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