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A Novel Approach for C–C, C–N, and C–O Bond Formation Reactions: A Facile Synthesis of Benzophenazine, Quinoxaline, and Phenoxazine Derivatives via Ring Opening of Benzoxepines
- Source :
- Organic Letters. 16:420-423
- Publication Year :
- 2013
- Publisher :
- American Chemical Society (ACS), 2013.
-
Abstract
- A new one-pot protocol has been developed for the synthesis of benzophenazine, quinoxaline, and phenoxazine derivatives by the reaction of benzoxepine-4-carboxylates with benzene-1,2-diamines, ethane-1,2-diamine, and 2-aminophenols in the presence of Bi(OTf)3 (5 mol %) under mild conditions in very good yields. The present protocol opens a new way for C-C, C-N, and C-O bond-formation reactions in a single-step process. The structural assignment was confirmed by X-ray analysis.
- Subjects :
- Mesylates
Ethane
Molecular Structure
Stereochemistry
Organic Chemistry
Carboxylic Acids
Chemistry, Organic
Diamines
Bond formation
Aminophenols
Ethylenediamines
Ring (chemistry)
Heterocyclic Compounds, 4 or More Rings
Biochemistry
Medicinal chemistry
chemistry.chemical_compound
Quinoxaline
chemistry
Cyclization
Quinoxalines
Oxazines
Benzoxepins
Phenazines
Physical and Theoretical Chemistry
Phenoxazine
Subjects
Details
- ISSN :
- 15237052 and 15237060
- Volume :
- 16
- Database :
- OpenAIRE
- Journal :
- Organic Letters
- Accession number :
- edsair.doi.dedup.....5e00666f0fc1838f54af8f27952526cb
- Full Text :
- https://doi.org/10.1021/ol4033122