One-Pot Synthesis of Chromone-Fused Pyrrolo[2,1-<i>a</i>]isoquinolines and Indolizino[8,7-<i>b</i>]indoles: Iodine-Promoted Oxidative [2 + 2 + 1] Annulation of <i>O</i>-Acetylphenoxyacrylates with Tetrahydroisoquinolines and Noreleagnines
Zhi‐Hao Shang, Xiangjin Zhang, Yi‐Ming Li, Ruixue Wu, Huiru Zhang, Lu-Ying Qin, Xue Ni, Yu Yan, An‐Xin Wu, Yanping Zhu
Abstract
An iodine-promoted one-pot cascade oxidative annulation reaction has been developed for the synthesis of chromone-fused-pyrrolo[2,1-a]isoquinolines and indolizino[8,7-b]indoles from o-acetylphenoxyacrylates, tetrahydroisoquinolines, and noreleagnines. This process underwent a logical approach to both chromone-fused-pyrrolo[2,1-a]isoquinolines and chromone-fused-indolizino[8,7-b]indoles isolamellarin derivatives. Manipulations of l-menthol and dl-α-tocopherol demonstrate the applications of this strategy.
Topics & Concepts
ChromoneChemistryAnnulationIodineStereochemistryOrganic chemistryMedicinal chemistryCatalysisSynthesis and Characterization of PyrrolesOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods