Environmental-benign oxidation of 2-oxazolines to oxazoles by dioxygen as the sole oxidant

• Published in: Tetrahedron Vol. 67; no. 11; pp. 2066 - 2071
• Main Authors: Huang, Yue, Ni, Lijun, Gan, Haifeng, He, Yu, Xu, Jinyi, Wu, Xiaoming, Yao, Hequan
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 18.03.2011; Elsevier
• Subjects: 2-Oxazolines; Antineoplastic agents; Biological and medical sciences; Chemistry; Chemistry, Organic; Conversion; Dioxygen; Environmental-benign; Exact sciences and technology; General aspects; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Inhibitors; Medical sciences; Organic chemistry; Oxazole; Oxazoles; Oxidants; Oxidation; Oxidizing agents; Pharmacology. Drug treatments; Physical Sciences; Preparations and properties; Science & Technology; Sole; Tetrahedrons; Oxidation; Oxazoles; 2-Oxazolines; Environmental-benign; Dioxygen; PEPTIDE ANTIBIOTICS; EPOTHILONE; PRODUCTS; BIOSYNTHESIS; ALDEHYDES; THIAZOLINES; PRECURSORS; Antineoplastic agent; Substituent effect; Enzyme; Phosphoric monoester hydrolases; Enzyme inhibitor; Oxazoline derivatives; Esterases; Oxidant; Oxygen molecules; N,N-Dimethylformamide; Hydrolases; Green chemistry; Chemical synthesis; Oxazole derivatives; Potassium carbonate; Oxygen nitrogen heterocycle; Protein-tyrosine-phosphatase
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.01.050

A facile and environment-benign oxidation by dioxygen as the sole oxidant was applied for the conversion of 2-oxazolines to oxazoles. The substituent effect on 2-oxazoline ring was investigated. The use of this methodology for the synthesis of a key intermediate of a CDC25 phosphatase inhibitor ( SC- ααδ9) as an anticancer agent was also described. [Display omitted]