Double Ring Expansion Strategy for Fused 3‑Benzazepines: Alternative Synthesis of the Dolby–Weinreb Enamine

A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with N-chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 87; no. 24; pp. 16947 - 16951
Main Authors Saito, Keigo, Aoyama, Hiroshi, Sako, Makoto, Arisawa, Mitsuhiro, Murai, Kenichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.12.2022
Amer Chemical Soc
Subjects
Alkaloids
Benzazepines
Chemistry
Chemistry, Organic
Molecular Structure
Physical Sciences
Science & Technology
REARRANGEMENT
AMINES
CEPHALOTAXINE
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Summary:A double ring expansion strategy for constructing fused 3-benzazepines is described. The oxidative ring expansion of spiroamine compounds with N-chlorosuccinimide and subsequent ring expansion of the resulting ketiminium ion intermediates with trimethylsilyldiazomethane afforded fused 3-benzazepines in a one-pot operation. Importantly, the Dolby–Weinreb enamine, which is a key synthetic intermediate for harringtonine alkaloids, cephalotaxines, can be accessed from commercial materials in only two steps using our developed method.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.2c02475