Efficient synthesis of 2,3-dihydro-1,4-benzoxazines via intramolecular copper-catalyzed O-arylation

Tetrahedron Letters

Volumn 50, Issue 27, 2009, Pages 3790-3793

  Liu, Zhangqin ^a,b   Chen, Yuanwei ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Benzoxazine; Copper; Intramolecular; O Arylation; Ullmann coupling

Indexed keywords

AMINOALCOHOL; BENZOXAZINE DERIVATIVE; COPPER;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 65549149477     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.055     Document Type: Article

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59. 3): δ 145.9, 137.8, 129.1, 122.0, 111.0, 85.1, 65.9, 51.5, 20.9.
60. Typical representative experimental procedure: NaOt-Bu (96 mg, 1 mmol), CuI (9.5 mg, 0.05 mmol), 1,10-phenanthroline (18 mg, 0.1 mmol), and 1a (155 mg, 0.5 mmol) were taken in a 10 ml round-bottomed flask. The flask was evacuated and back-filled with nitrogen three times. Dry dioxane (2 ml) was added to the mixture at room temperature. The resulting mixture was placed at oil base, and heated for 24 h at 100 °C. after complete disappearance of 1a (TLC), the reaction mixture was allowed to cool to room temperature and the solvent was evaporated. The mixture was purified by flash chromatography on silica gel using ethyl acetate/petroleum ether as eluent to give white solid 2a (79 mg, 86%).
61. 10NOCl: 183.0529; found: 184.0518 [M+H].