Relay Cu(I)/Brønsted Base Catalysis for <i>Phospha</i>‐Michael Addition/5‐<i>exo</i>‐<i>dig</i> Cyclization/Isomerization of <i>in</i> <i>situ</i> Formed <i>aza</i>‐Alkynyl <i>o‐</i>quinone methides with P(O)−H compounds to C3‐Phosphorylated Indoles
Long Chen, Xiaoyan Liu, Jing Zhang, Li Duan, Zhong Wen, Hai‐Liang Ni
Abstract
Abstract A relay Cu(I)/Brønsted base catalyzed one‐pot phospha ‐Michael addition/5‐ exo ‐ dig cyclization/isomerization of in situ generated aza ‐alkynyl o ‐quinone methides ( N ‐ o ‐AQMs) from 1‐( o ‐aminophenyl)prop‐2‐ynols with P(O)‐compounds has been established to afford C3‐phosphorylated indoles. It demonstrates that the 1,4‐conjugate addition adduct from N ‐ o ‐AQMs could undergo further cyclization with the tethered alkyne moiety to afford N ‐heterocyclic compounds. magnified image
Topics & Concepts
IsomerizationChemistryMoietyAdductDigAlkyneMichael reactionIn situConjugateCatalysisCycloisomerizationMedicinal chemistryBase (topology)StereochemistryOrganic chemistryMathematical analysisComputer scienceMathematicsComputer securitySynthesis of Indole DerivativesCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques