Reductions of (1R,3R,4R)-3-([1,2,4]triazolo[4,3-x]azin-3-yl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ones and their analogues |
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| Institution: | 1. K?rklareli University, Faculty of Technology, Department of Energy Systems Engineering, 39000 K?rklareli, Turkey;2. Eski?ehir Osmangazi University, Faculty of Arts and Sciences, Department of Chemistry, 26480 Eski?ehir, Turkey;3. Gebze Technical University, Department of Chemistry, 41400 Gebze, Turkey;1. National Taras Shevchenko University of Kyiv, Volodymyrska Street 64, Kyiv 01601, Ukraine;2. Enamine Ltd, Alexandra Matrosova Street 23, Kyiv 01103, Ukraine;3. STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, Lenina ave. 60, 61001 Kharkiv, Ukraine;1. Department of Biology, Georgia State University, Atlanta, GA 30303, USA;2. Department of Computer Science, Georgia State University, Atlanta, GA 30303, USA;3. Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA;1. Laboratory of Pharmaceutical Design & Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, China;2. College of Forestry, Northwest A&F University, Yangling 712100, Shaanxi Province, China;1. The College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000, PR China;2. The College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan 450052, PR China |
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| Abstract: | Reductions of (1R,3R,4R)-3-(1,2,4]triazolo4,3-x]azin-3-yl)-1,7,7-trimethylbicyclo2.2.1]heptan-2-ones and their lactone analogues, prepared from (1R)-(+)-camphor, were studied. Catalytic hydrogenation selectively led to partial saturation of the 1,2,4]triazolo4,3-x]azine residue, while in reactions with borane–methylsulfide coordination of borane to the 1-position of 1,2,4]triazolo4,3-x]azine system took place. On the other hand, activation of the carbonyl group in (1R,3R,4R)-3-(1,2,4]triazolo4,3-x]azin-3-yl)-1,7,7-trimethylbicyclo2.2.1]heptan-2-ones with boron trifluoride etherate followed by reaction with borane–methylsulfide furnished the corresponding isoborneols, stereoselectively. The structures of all representative compounds were confirmed by X-ray diffraction. |
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