Regioselective Synthesis of Trisubstituted Quinoxalines Mediated by Hypervalent Iodine Reagents

• Published in: Journal of organic chemistry Vol. 86; no. 23; pp. 16892 - 16900
• Main Authors: Suzuki, Yumiko, Takehara, Ren, Miura, Kasumi, Ito, Ryota, Suzuki, Noriyuki
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 03.12.2021; American Chemical Society (ACS); Amer Chemical Soc
• Subjects: achieved using; afford trisubstituted quinoxalines; Biochemistry; Biotechnology; Cancer; Chemical Sciences not elsewhere classified; Chemistry; Chemistry, Organic; Computational Biology; Developmental Biology; Environmental Sciences not elsewhere classified; excellent regioselectivities; hypervalent iodine reagents; Immunology; important motif; Indicators and Reagents; Iodides; Iodine; materials sciences; medicinal chemistry; Medicine; organic chemistry; Pharmacology; phenylenediamines; Physical Sciences; previously established; Prospective Studies; prospective utility; Quinoxalines; regioselective manner; regioselective preparation; regioselective synthesis; regioselectivity; reported system; Science & Technology; Science Policy; trisubstituted quinoxalines; trisubstituted quinoxalines mediated; OXIDATION; MOLECULAR-IODINE; ONE-POT SYNTHESIS; ANNULATION; CATALYZED SYNTHESIS; EXPEDIENT SYNTHESIS; EFFICIENT SYNTHESIS; PROTOCOL; DERIVATIVES; UNSYMMETRICAL BENZILS
• ISSN: 0022-3263; 1520-6904; 1520-6904
• DOI: 10.1021/acs.joc.1c02087

A facile and regioselective synthesis of quinoxalines, an important motif in medicinal chemistry and materials sciences, was developed. Despite their prospective utility, the regioselective preparation of trisubstituted quinoxalines has not been previously established. In the reported system, hypervalent iodine reagents catalyzed the annulation between α-iminoethanones and o-phenylenediamines in a chemo/regioselective manner to afford trisubstituted quinoxalines. Excellent regioselectivities (6:1 to 1:0) were achieved using [bis­(trifluoroacetoxy)­iodo]­benzene and [bis­(trifluoroacetoxy)­iodo]­penta­fluorobenzene as annulation catalysts.