Domino Aryne Annulation via a Nucleophilic–Ene Process
摘要:
1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.
Stereoselective Synthesis of Tetrahydroquinolines Through an Imino-Ene Cyclization Reaction
作者:Somasekhar Bondalapati、Kiran Indukuri、Priya Ghosh、Anil K. Saikia
DOI:10.1002/ejoc.201201363
日期:2013.2
heterocycles by using the oxonium-ene and thionium-ene cyclizationreaction, respectively. Herein, we report amethodology for the synthesis of tetrahydroquinolines. Thereaction between an aldehyde and α-allylic aniline proceedsthrough an imino-enecyclization that is mediated by borontrifluoride–diethyl ether.
the counterion (I−, BF), a reductive cleavage of the N(1)–C(8a) bond (photo-Emde degradation). The corresponding N,N-dimethyl-3-phenylpropylamines are formed in high yields and without contamination by Hofmann degradation products of the tetrahydroquinolinium salts. Me groups at C(2) as well as substituents at C(6) (CH3, Cl, CH3O) favour the photo-Emde degradation. The aromatic Cl-substituent is reductively