Transition-Metal-Free Tandem Oxidative Removal of Benzylic Methylene Group by C–C and C–N Bond Cleavage Followed by Intramolecular New Aryl C–N Bond Formation under Radical Conditions

Transition-Metal-Free Tandem Oxidative Removal of Benzylic Methylene Group by C–C and C–N Bond Cleavage Followed by Intramolecular New Aryl C–N Bond Formation under Radical Conditions

A novel tandem oxidative conversion of 10,11-dihydro-5H-dibenzo­[b,e]­[1,4]­diazepines to phenazines has been achieved under transition-metal-free, mild conditions using K2S2O8 or DDQ as the oxidizing agent. The transformation proceeds through oxidative removal of a benzylic methylene group by C–C a...

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Bibliographic Details
Published in:Organic letters Vol. 16; no. 17; pp. 4392 - 4395
Main Authors: Laha, Joydev K, Tummalapalli, K. S. Satyanarayana, Gupta, Ankur
Format: Journal Article
Language:English
Published: United States American Chemical Society 05-09-2014
Subjects:
Catalysis
Dibenzazepines - chemistry
Molecular Structure
Oxidation-Reduction
Phenazines - chemical synthesis
Phenazines - chemistry
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Summary:A novel tandem oxidative conversion of 10,11-dihydro-5H-dibenzo­[b,e]­[1,4]­diazepines to phenazines has been achieved under transition-metal-free, mild conditions using K2S2O8 or DDQ as the oxidizing agent. The transformation proceeds through oxidative removal of a benzylic methylene group by C–C and C–N bond cleavage followed by a new aryl C–N bond formation under radical conditions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol501766m