Addition of nitrogen dioxide to carbon-carbon double bond followed by a cyclization to construct nitromethylated
Xuanxuan Li1, Shengyi Zhuang1, Xinxin Fang1
1College of Chemistry and Materials Science, Nanjing Normal University; Jiangsu Provincial Key Laboratory of Material Cycle Processes and Pollution Control; Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing 210023, China. sunpeipei@njnu.edu.cn.
Abstract:
Heterocyclic derivatives 4-(nitromethyl)isoquinoline-1,3(2H,4H)-diones were synthesized via a tandem nitration/cyclization reaction of N-alkyl-N-methacryloyl benzamides under metal-free conditions. The cheap and available reagent nitrogen dioxide was used as the nitro source, as well as the oxidant. For the substrates with various substituent groups, the reaction proceeded smoothly to give the corresponding isoquinolinedione derivatives in moderate to good yields. The products could be converted into aminomethyl or hydroxyl substituted heterocyclic derivatives by the simple reduction.
Related Concept Videos
Preparation of Nitriles
Nitrosation of Enols
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
2° Amines to N-Nitrosamines: Reaction with NaNO2
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3


![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)