Dibenzoxazepinium Ylides: Facile Access and 1,3-Dipolar Cycloaddition Reactions

被引：30

作者：

Khlebnikov, Alexander F. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Petrovskii, Petr P. ^{[1
]}

Magull, Joerg ^{[2
]}

Ringe, Arne ^{[2
]}

机构：

[1] St Petersburg State Univ, Dept Chem, St Petersburg 198504, Russia

[2] Univ Gottingen, Inst Inorgan Chem, Gottingen, Germany

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

关键词：

SUBSTITUTED AZOMETHINE YLIDES; HIV-1; REVERSE-TRANSCRIPTASE; HALOGENATED IMINO COMPOUNDS; POTENT PGE(2) ANTAGONIST; REACTIVITY; DIFLUORO; DIACYLHYDRAZINE; ANTICONVULSANT; FLUOROCARBENE; GENERATION;

D O I：

10.1021/ol802813a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective approach to azirino-fused heterocycles is disclosed. The approach, involving formation of heterocycle/C-(arylchloromethyl)-subsituted C=N 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 C=C dipolarophiles giving derivatives of dibenzo[b,f]pyrrolo[1,2-d][1,4]oxazepine.

引用

页码：979 / 982

页数：4

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