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

被引：43
|
作者：
Laha, Joydev K. [1 ]
Tummalapalli, K. S. Satyanarayana [1 ]
Gupta, Ankur [1 ]
机构：
[1] Natl Inst Pharmaceut Educ & Res, Dept Pharmaceut Technol Proc Chem, Sas Nagar 160062, Punjab, India
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 17期
关键词：
CARBON-NITROGEN BOND; ALIPHATIC CARBOXYLIC-ACIDS; SECONDARY-AMINES; 2-ARYL BENZOTHIAZOLES; KETONES; AMIDES; TRANSFORMATION; CONDENSATION;
D O I：
10.1021/ol501766m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：4392 / 4395
页数：4
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