Related Experiment Video
Updated: Jun 26, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Dibenzoxazepinium ylides: facile access and 1,3-dipolar cycloaddition reactions
Alexander F Khlebnikov1, Mikhail S Novikov, Petr P Petrovskii
1Department of Chemistry, St. Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, Russia. alexander.khlebnikov@pobox.spbu.ru
Abstract:
An effective approach to azirino-fused heterocycles is disclosed. The approach, involving formation of heterocycle/C-(arylchloromethyl)-subsituted CN double bond via domino isomerization of a gem-dichloroaziridine-intramolecular Friedel-Crafts acylation of the O-tethered benzene ring and subsequent intramolecular cyclization induced by hydride, was realized for 1-aryl-1,11b-dihydroazirino[1,2-d]dibenz[b,f][1,4]oxazepines. The latter are excellent precursors of azomethine ylides, especially in solvent-free conditions, which can undergo a completely stereoselective 1,3-dipolar cycloaddition to CC dipolarophiles giving derivatives of dibenzo[b,f]pyrrolo[1,2-d][1,4]oxazepine.
Related Concept Videos
Cycloaddition Reactions: Overview
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
