利用親電性環化反應高效率地合成benzoxazine衍生物

Highly efficient synthesis of 4H-3,1-benzoxazines by the electrophilic cyclization reaction

沈鶴全(Ho-Chuan Shen)

指導教授 ： 王志鉦

高雄醫學大學/生命科學院/醫藥暨應用化學研究所/碩士(2010年)

https://doi.org/10.6832/KMU.2010.00139

摘要

4H-3,1-benzoxazin的結構類似物，在許多文獻中顯示各種衍生物的重要生物活性，被用來殺菌，除草，消炎藥，抗驚厥[1]，以及DNA結合抗腫瘤試劑[9]。設計用(2-phenylethynyl-phenyl)-methanone化合物為起始物，以碘分子為親電性試劑進行分子內環化反應，而得到高產率的4H-3,1-benzoxazin為主體的衍生物，期待能有相關生物活性表現。

關鍵字

親電性 ； 環化反應

並列摘要

4H-3,1-Benzoxazine derivatives displays important biological activities in many research announcements, that have been used as fungicidal,herbicidal, anticonvulsant, anti-inflammatory agents and as DNA-binding antitumor agents. In this thesis ,we studied design intramolecular 6-endo-dig electrophilic cyclization of N-(2-Phenylethynyl-phenyl)-benzamide compounds by iodine reagents. The reaction afforded 4H-3,1-benzoxazin derivatives in good yields with various functional groups.

並列關鍵字

electrophilic ； cyclization ； benzoxazine

參考文獻

1. P. He; J. Wu; Y. B. Nie; M. W. Ding, Tetrahedron 2009, 65, 8563–8570.

2. P. W. Hsieh; F. R. Chang; C. H. Chang; P. W. Cheng; L. C. Chiang; F. L. Zeng; K. H. Lind and Y. C. Wu., Bioorg. Med. Chem. Lett. 2004, 14, 4751.

3. (a) M. Gutschow; L. Kuerschner; U. Neumann; M. Pietsch; R. Loser; N. Koglin and K. Eger., J. Med. Chem. 1999, 42, 5437. (b) A. Krantz; R. W. Spencer; T. F. Tam; T. J. Liak; L. J. Copp; E. M. Thomas and S. P. Rafferty., J. Med. Chem. 1990, 33, 464.

4. M. Gutschow and U. Neumann, Bioorg. Med. Chem. 1997, 5, 1935.

5. (a) U. Neumann; M. Gutschow, Bioorg. Chem. 1995, 23, 72. (b) L. Hedstrom; A. R. Moorman; J. Dobbs; R. H. Abeles, Biochemistry 1984, 23, 1753.