Metal-free regioselective nitration of quinoxalin-2(1H)-ones with tert-butyl nitrite. Issue 48 (2nd December 2021)

• Record Type: Journal Article
• Authors: Li, Yi-Na; Li, Xue-Lin; Wu, Jin-Bo; Jiang, Hong; Liu, Yunmei; Guo, Yu; Zeng, Yao-Fu; Wang, Zhen
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 48(2021)
• Page Start: 10554
• Page End: 10559
• Publication Date: 2021-12-02
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02015c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A metal-free regioselective nitration of quinoxalin-2(1 H )-ones at the C5 or C7 position has been established, which was distinct from the previous functionalization of quinoxalin-2(1 H )-ones. Abstract : A metal-free coupling of quinoxalin-2(1 H )-ones with tert -butyl nitrite has been developed. Distinctly from the previous functionalization of quinoxalin-2(1 H )-ones, this nitration reaction took place selectively at the C7 or C5 position of the phenyl ring, affording a series of 7-nitro and 5-nitro quinoxalin-2(1 H )-ones in moderate to good yields. Preliminary mechanistic studies revealed that the reaction may involve a radical process.