{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["8(25)"],"submitter":["Zhang X"],"pubmed_abstract":["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."],"journal":["ACS omega"],"pagination":["22352-22360"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC10308564"],"repository":["biostudies-literature"],"pubmed_title":["Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-<i>ortho</i>-quinone Methide Precursor."],"pmcid":["PMC10308564"],"pubmed_authors":["Gan S","Shao H","Li Z","Wang C","Zhang X","Wang W","Gou Z","Xing Q"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis of Functionalized Tetrahydroquinoline Containing Indole Scaffold via Chemoselective Annulation of Aza-<i>ortho</i>-quinone Methide Precursor.","description":"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.","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Jun","modification":"2025-04-19T07:31:48.621Z","creation":"2025-04-19T07:31:48.621Z"},"accession":"S-EPMC10308564","cross_references":{"pubmed":["37396238"],"doi":["10.1021/acsomega.2c07036"]}}