Dibenzoxazepinium ylides: facile access and 1,3-dipolar cycloaddition reactions.
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.
Khlebnikov
Alexander F
AF
Department of Chemistry, St. Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, Russia. alexander.khlebnikov@pobox.spbu.ru
Novikov
Mikhail S
MS
Petrovskii
Petr P
PP
Magull
Joerg
J
Ringe
Arne
A
D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010077:Oxazepines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D001391:Azo Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; D010077:Oxazepines; D011758:Pyrroles