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Synfacts 2013; 9(1): 0030
DOI: 10.1055/s-0032-1317878
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Synthesis of Benzo[b][1,4]oxazepines

Contributor(s):
Victor Snieckus
,
Matthew O. Kitching
Liu B, Li Y, Yin M, Wu W, Jiang H * South China University of Technology, Guangzhou, P. R. of China
Palladium-Catalyzed Tandem Reaction of o-Aminophenols, Bromoalkynes and Isocyanides to Give 4-Amine-benzo[b][1,4]oxazepines.

Chem. Commun. 2012;
48: 11446-11448
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

benzo[b][1,4]oxazepines - domino reaction - palladium - bromoalkynes - isocyanides

Significance

Reported is the palladium-catalyzed synthesis of benzo[b][1,4]oxazepines 4 via the annulation of o-aminophenols 1 with bromo­alkynes 2 and isocyanides 3. Substrate-scope investigation revealed broad tolerance to variation of all components 1–3, particularly across sterically and electronically differentiated aryl bromoalkynes 2, with a reduction in yield noted for alkyl bromo­alkynes (4o). Experiments demonstrating the competency of 5 under the standard reaction conditions are offered in support of the proposed mechanism.


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Comment

Building on their previous investigations into combining the nucleophilic addition of isocyanides 3 to bromoalkynes 2 with palladium catalysis (Chem. Commun. 2012, 48, 3545), the current report extends this methodology allowing the synthesis of benzoazepines traditionally synthesized by multiple-step procedures. Taking advantage of the established addition of phenols to bromoalkynes (For furan synthesis, see: S. Wang et al. Org. Lett. 2011, 13, 5968) the current report, intercepting intermediate 5, appears to have exceptional scope.


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