Synlett 2018; 29(05): 597-602
DOI: 10.1055/s-0036-1589139
letter
© Georg Thieme Verlag Stuttgart · New York

Mild and Direct C–H Arylation of Quinoxalin-2(1H)-ones with Aryldiazonium Salts under Metal-Free Conditions

Kun Yin
a  School of Chemical Science and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China
,
a  School of Chemical Science and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China
b  Shanghai Key Lab of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, P. R. of China   Email: rhzhang@tongji.edu.cn
› Author Affiliations
Financial support from the National Nature Science Foundation of China (20972113/B020502) is gratefully acknowledged.
Further Information

Publication History

Received: 12 September 2017

Accepted after revision: 29 October 2017

Publication Date:
11 December 2017 (online)

Abstract

A mild and direct C–H arylation of quinoxazolin-2(1H)-ones with aryldiazonium salts has been developed. A wide variety of 3-arylquinoxazolin-2(1H)-ones were synthesized in up to 92% yield at room temperature under metal-free conditions. This strategy tolerates a wide range of functional groups and shows environmental friendliness and practicality.

Supporting Information

 
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  • 13 1-Methyl-3-(4-phenoxyphenyl)quinoxalin-2(1H)-one (3h); Typical Procedure A 25 mL round bottle was charged with 4-phenoxyaniline (4.0 equiv) and anhyd MeCN (1.0 mL). t-BuONO (6.0 equiv) was added dropwise from a syringe cooled in an ice bath, and the syringe was then rinsed through with MeCN (2 × 0.5 mL). When the addition was complete, the mixture was warmed to r.t. and stirred for 0.5 h to form 4-PhOC6H4N=NOBu-t in situ. The mixture was then transferred to an oven-dried 25 mL Schlenk tube containing 1-methylquinoxalin-2(1H)-one (1a; 0.3 mmol, 1.0 equiv). The bottle was rinsed with MeCN (2 × 0.5 mL), which was also transferred into the Schlenk tube. The atmosphere in the Schlenk tube was then exchanged adequately by N2 and the mixture was stirred for 48 h at r.t. The final mixture was diluted with EtOAc and filtered through a pad of silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by TLC [self-prepared silica gel plates, PE­–EtOAc (20:1 to 10:1)] to give an orange solid; yield: 70 mg (71%); mp 102–104 °C. 1H NMR (400 MHz, CDCl3): δ = 8.40–8.33 (m, 2 H), 7.93 (dd, J = 8.0, 1.6 Hz, 1 H), 7.60–7.53 (m, 1 H), 7.42–7.31 (m, 4 H), 7.15 (t, J = 7.4 Hz, 1 H), 7.11–7.07 (m, 4 H), 3.78 (s, 3 H). 13C NMR (101 MHz, CDCl3): δ = 159.50, 156.56, 154.80, 153.16, 133.27, 133.16, 131.56, 130.97, 130.32, 130.14, 129.92, 123.88, 123.80, 119.61, 117.89, 113.64, 29.37. HRMS (ESI): m/z [M + H]+ calcd for C21H17N2O2: 329.1285; found: 329.1276.
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