Herein, we evolve a base-promoted synthesis of 2-chromen-2-one and chromeno[2,3-]pyrrole scaffolds via (4 + 2) annulation of α-alkylidene succinimides with 2-hydroxyphenyl-substituted -quinone methides (-QMs). Extremely selective and switchable cyclizations were obtained by modifying the base. This metal-free protocol is highlighted by its mild reaction conditions and broad substrate scope, and the viability of the existing protocol was additionally illustrated by gram-scale synthesis and further modification. Several control experiments were performed to understand the reaction mechanism.
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Cascade Annulation for Synthesizing Chromenopyrrolones from -Hydroxyphenyl Enaminones and 2-Halo--alkyloxyacetamides.
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A cascade cyclization reaction comprising two halogenation reactions and a Michael addition was developed for the synthesis of chromeno[2,3-]pyrrole-3-ones . Additionally, another cascade cyclization reaction, which involves a halogenation reaction followed by two intramolecular Michael additions, was established for the synthesis of chromeno[2,3-]pyrrole-2-ones . Both types of compounds were synthesized from -hydroxyphenyl enaminones and 2-halo--alkyloxyacetamides through a process that facilitated the intramolecular formation of C-C, C-O, and C-N bonds to effectively establish two fused rings in a single operation.
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