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Two complementary cascade cyclization reactions were described, namely KHSO4-promoted [1+2+3] cyclization and TMSCl-promoted four-molecular cascade cyclization for the concise synthesis of highly functionalized spirooxindoles in excellent yields. Between them, the… Click to show full abstract
Two complementary cascade cyclization reactions were described, namely KHSO4-promoted [1+2+3] cyclization and TMSCl-promoted four-molecular cascade cyclization for the concise synthesis of highly functionalized spirooxindoles in excellent yields. Between them, the improved TMSCl-promoted cyclization reaction of isatins, N,N-dimethylenaminones and amines was carried out to afford various desired products under milder conditions. The observed chemoselectivity of new TMSCl-promoted cyclization mechanism was reasonably explained by designing the intermediate bis-enaminones. Furthermore, the gram-scale synthesis and the synthetic applications were also evaluated.
Journal Title: European Journal of Organic Chemistry
Year Published: 2017
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