Syntheses of 3-Aryl Tetrahydroisoquinolines via an Intermolecular [4 + 2] Cycloaddition of Sultines with Imines

Organic Letters, Год журнала: 2022, Номер 24(23), С. 4192 - 4196

Опубликована: Май 31, 2022

The development of an intermolecular aza-Diels–Alder (DA) cycloaddition sultines and imines is reported. By exploiting as o-quinodimethane precursors aryl dienophiles in the presence Cu(OTf)2, aza-DA reaction proceeds to provide a wide variety 3-aryl tetrahydroisoquionlines moderate excellent yield (up 89%). synthetic utility these products was demonstrated preparation tetracyclic N-heterocycles, including tetrahydroprotoberberine skeleton.

Язык: Английский

Route to Functionalized Tetrahydrobenzo[d]azepines via Re₂O₇-Mediated Intramolecular Friedel–Crafts Reaction

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 2001 - 2008

Опубликована: Янв. 22, 2024

We describe a Re2O7-mediated intramolecular dehydrative Friedel–Crafts reaction for the efficient synthesis of various benzo-fused heterocycles such as benzazepines and benzazocines. This process is characterized by broad substrate scope, mild conditions, high efficiency, atom economy. The potential application this methodology was exemplified facile preparation NMDA antagonist well key intermediate en route to SKF 38393.

Язык: Английский

Seven-membered rings

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 569 - 628

Опубликована: Янв. 1, 2023

Язык: Английский