Controllable Synthesis of <i>N</i>-Heterocycles via Hydride Transfer Strategy-Enabled Formal [5 + 1] and [5 + 2] Cyclizations
Ying Dong, Fangzhi Hu, Huixin Wu, Feng-Wei Guo, Liang Wang, Feng‐Yu Du, Shuai‐Shuai Li
Abstract
The Brønsted acid-controlled switchable synthesis of indoline-fused tetrahydroquinolines and indole-fused benzazepines was developed through hydride transfer-enabled formal [5 + 1] and [5 + 2] cyclization reactions from indoles and N- alkyl o -aminobenzoketones. Indoline, furanone, and tetrahydroquinoline hybridized pentacyclic products were unprecedentedly accessed via a cascade condensation/hydride transfer/dearomatization-cyclization/deethylation/nucleophilic addition process. In addition, the undeveloped hydride transfer-involved [5 + 2] cyclizations were also realized for direct construction of indole-fused benzazepines.
Topics & Concepts
ChemistryBenzazepinesIndolineHydrideIndole testNucleophileCombinatorial chemistryNucleophilic additionAlkylCascadeOrganic chemistryCatalysisHydrogenChromatographyCatalytic C–H Functionalization MethodsChemical synthesis and alkaloidsAlkaloids: synthesis and pharmacology