[3-硝基亚苄基-2,3(3H,5H)-呋喃二酮在汉茨希吡啶合成中的应用。1. 呋喃并(3,4-b)吡啶的一种新合成方法]
[3-nitrobenzylidene-2,3(3H,5H)-furandione in the Hantzsch pyridine synthesis. 1. A new approach to furo(3,4-b)pyridines].
作者信息
Görlitzer K, Bartke U
机构信息
Institut für Pharmazeutische Chemie, Technischen Universität Braunschweig, Germany.
出版信息
Pharmazie. 2002 Oct;57(10):672-8.
The nitrobenzylidenefurandiones 7 react with acetoacetic ester (8) and ammonium acetate or 3-aminocrotonic esters (9a, b) and 2-amino-pent-2-en-4-on (9c), respectively heating in acetic acid to yield the tetrahydrofuro[3,4-b]pyridines 10. The dehydrogenation of 10 using nitric acid or activated manganese dioxide leads to the dihydrofuro[3,4-b]pyridines 12. When the reaction is carried out with the tetronic acid derivatives 7 and the enaminocarbonyl compounds 9 at 30 degrees C in tert-butanol the hexahydro-7a-hydroxyfuro[3,4-b]pyridines 11 are obtained. Treating the N,O-acetales 11 with acetic anhydride in pyridine affords the annulated lactones 10.
硝基亚苄基呋喃二酮7分别与乙酰乙酸乙酯（8）和乙酸铵或3-氨基巴豆酸酯（9a、b）以及2-氨基戊-2-烯-4-酮（9c）在乙酸中加热反应，生成四氢呋喃并[3,4 - b]吡啶10。使用硝酸或活性二氧化锰对10进行脱氢反应，得到二氢呋喃并[3,4 - b]吡啶12。当硝基亚苄基呋喃二酮7与烯胺羰基化合物9在叔丁醇中于30℃进行反应时，可得到六氢-7a - 羟基呋喃并[3,4 - b]吡啶11。在吡啶中用乙酸酐处理N,O - 缩醛11，得到稠合内酯10。
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