Two novel and highly efficient solid support (SS) versions of tetrahydroquinoline synthesis based on the three component condensation reaction of aldehydes, anilines, and electron-rich olefins catalyzed by trifluoroacetic acid were described. In the first version, 4-carboxybenzaldehyde was immobilized on Acid sensitive MEthoxy Benz Aldehyde ( AMEBA) resin as the solid-supported component of this reaction. The procedure provided tetrahydroquinolines in high yield (60–80%) and good purity (>80%). Further advancement of this solid-phase synthesis was achieved by using resin-bound olefins (prepared from immobilized 4-hydroxybenzaldehyde, and the corresponding Wittig reagents) with anilines, and aldehydes to afford the target products (61–85% yields, >85% purity). Both SS approaches allowed the use of novel alkene, aniline, and aldehyde entries, thereby yielding a diverse array of tetrahydroquinolines.
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