Addition of nitrogen dioxide to carbon–carbon double bond followed by a cyclization to construct nitromethylated isoquinolinediones. Issue 8 (3rd February 2017)

• Record Type: Journal Article
• Authors: Li, Xuanxuan; Zhuang, Shengyi; Fang, Xinxin; Liu, Ping; Sun, Peipei
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 8(2017)
• Page Start: 1821
• Page End: 1827
• Publication Date: 2017-02-03
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02797k
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : 4-(Nitromethyl)isoquinoline-1, 3(2 H, 4 H )-diones were synthesized via a tandem nitration/cyclization reaction of N -alkyl- N -methacryloyl benzamides using CO2 as the nitro source. Abstract : Heterocyclic derivatives 4-(nitromethyl)isoquinoline-1, 3(2 H, 4 H )-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.