Lawesson's reagent-initiated domino reaction of aminopropenoyl cyclopropanes: synthesis of thieno[3,2-c]pyridinones |
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| Authors: | Huang Peng Zhang Rui Liang Yongjiu Dong Dewen |
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| Institution: | Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China. |
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| Abstract: | A convenient and efficient synthesis of substituted 2,3-dihydrothieno3,2-c]pyridin-4(5H)-ones has been developed and relies upon a domino reaction of dimethylaminopropenoyl cyclopropanes initiated by Lawesson's reagent. A mechanism involving regioselective thionation, ring-enlargement, and an intramolecular aza-cyclization sequence is proposed. This protocol was utilized as a one-pot route to thieno3,2-c]pyridin-4(5H)-ones with DDQ as an oxidant. |
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