biostudies-literatureUnknown8(25)Zhang XThe chemoselective annulation of aza-<i>ortho</i>-quinone methide generated by in situ <i>o</i>-chloromethyl sulfonamide has been achieved with bifunctional acyclic olefin. This efficient approach provides access to the diastereoselective synthesis of functionalized tetrahydroquinoline derivatives containing indole scaffolds through the inverse-electron-demand aza-Diels-Alder reaction under mild reaction conditions with excellent results (up to 93% yield, > 20:1 dr). Moreover, this article realized the cyclization of α-halogeno hydrazone with electron-deficient alkene affording the tetrahydropyridazine derivatives, which had never been reported.ACS omega22352-22360https://www.ebi.ac.uk/biostudies/studies/S-EPMC10308564biostudies-literatureSynthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-<i>ortho</i>-quinone Methide Precursor.PMC10308564Gan SShao HLi ZWang CZhang XWang WGou ZXing QfalseSynthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-<i>ortho</i>-quinone Methide Precursor.The chemoselective annulation of aza-<i>ortho</i>-quinone methide generated by in situ <i>o</i>-chloromethyl sulfonamide has been achieved with bifunctional acyclic olefin. This efficient approach provides access to the diastereoselective synthesis of functionalized tetrahydroquinoline derivatives containing indole scaffolds through the inverse-electron-demand aza-Diels-Alder reaction under mild reaction conditions with excellent results (up to 93% yield, > 20:1 dr). Moreover, this article realized the cyclization of α-halogeno hydrazone with electron-deficient alkene affording the tetrahydropyridazine derivatives, which had never been reported.2023-01-01T00:00:00Z2023 Jun2025-04-19T07:31:48.621Z2025-04-19T07:31:48.621ZS-EPMC103085643739623810.1021/acsomega.2c07036