| Studies on the esterifications of 9-（hydroxyimino）-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one with acid chlorides under different conditions |
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| 引用本文： | Ru Shu Sun Yang Wang Peng Xia. Studies on the esterifications of 9-（hydroxyimino）-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one with acid chlorides under different conditions[J]. 中国化学快报, 2008, 19(7): 791-794. DOI: 10.1016/j.cclet.2008.04.038 |
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| 作者姓名： | Ru Shu Sun Yang Wang Peng Xia |
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| 作者单位： | Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 200032, China |
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| 摘 要： | The esterifications of 9-（hydroxyimino）-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one （4） with acid chlorides afforded normal oxime-esters 3a-e in 35-78% yields in presence of excessive 4-dimethylaminopyridine as the acid scavenger, whereas the reactions gave unexpected 8-substituted products N-（8-chloro-4-methyl-2-oxo-2H-furo-[2,3-h]chromen-9-yl）amides （5a-c） and 4-methyl-2,9-dioxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-ylcarboxyloates （6d-e） by using excessive acid chlorides. The structures of 10 new compounds were determined by 1H NMR, 13C NMR, MS and HRMS, and the possible mechanism for the formation of unexpected products 5a--c and 6d-e was also proposed.
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| 关 键 词： | 酯化作用 酰基氯 合成 有机化学反应 |
Studies on the esterifications of 9-(hydroxyimino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one with acid chlorides under different conditions |
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| Ru Shu Sun,Yang Wang,Peng Xia. Studies on the esterifications of 9-(hydroxyimino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one with acid chlorides under different conditions[J]. Chinese Chemical Letters, 2008, 19(7): 791-794. DOI: 10.1016/j.cclet.2008.04.038 |
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| Authors: | Ru Shu Sun Yang Wang Peng Xia |
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| Affiliation: | Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 200032, China |
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| Abstract: | The esterifications of 9-(hydroxyimino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one (4) with acid chlorides afforded normal oxime-esters 3a-e in 35-78% yields in presence of excessive 4-dimethylaminopyridine as the acid scavenger,whereas the reactions gave unexpected 8-substituted products N-(8-chloro-4-methyl-2-oxo-2H-furo-[2,3-h]chromen-9-y1)amides (5a-c)and 4-methyl-2,9-dioxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-ylcarboxyloates (6d-e) by using excessive acid chlorides.The structures of 10 new compounds were determined by 1H NMR,13C NMR,MS and HRMS,and the possible mechanism for the formation of unexpected products 5a-e and 6d-e was also proposed. |
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| Keywords: | 9-(Hydroxyimino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one Oxime-ester N-(8-Chloro-4-methyl-2-oxo-2H-furo[2,3-h]chromen-9-y1)amide 4-Methyl-2,9-dioxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-ylcarboxyloate |
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