Synthesis of (1R,4E,5S)-4-{[(E)-(azinyl)diazenyl]methylidene}-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones and (1R,4R,5R)-4-([1,2,4]triazolo[4,3-x]azin-3-yl)-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones |
| |
| Affiliation: | 1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, PR China;2. Jiangsu Chia Tai Qingjiang Pharmaceutical Co., Ltd, PR China;3. Department of Chemical and Pharmaceutical Engineering of Southeast University Chengxian College, Nanjing 210088, PR China;1. Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland;2. Department of Chemistry, University of Wrocław, F. Joliot-Curie St. 14, 50-383 Wrocław, Poland;3. Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland;1. College of Chemistry and Materials, South-Central University for Nationalities, Wuhan, China;2. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, China |
| |
| Abstract: | 4-[(Heteroaryldiazenyl)methylidene] and 4-([1,2,4]triazolo[4,3-x]azin-3-yl) substituted (1R,5R)-4-1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-ones 6/6′ and 7/7′ were obtained in a one-pot transformation of the enamino lactone 2 with hydrazinoazines 3a–g followed by oxidation of the intermediate mixture of isomeric enehydrazines 4/4′ and hydrazones 5/5′ with lead tetraacetate. The oxidation selectivity was dependent on the ratio of isomeric intermediates 4/4′ and 5/5′. Treatment of 7b with lead tetraacetate led to α-acetoxylated compound 11, while bromination of 9b afforded a 1:1 mixture of α-bromination products 12 and 12′, which were separated by medium pressure liquid chromatography (MPLC). The structures of intermediates and products were confirmed by NMR and X-ray diffraction. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
