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3,4,5-Trimethoxybenzaldehyde(TMB)isimportantintermediateforthesynthesisofTMPanditisalsothestaFtingmaterialofthesynthesisof3,4,5-trimethoxycinnamide,whichwasusedasanticonvulsantmedicine'.ThetropolonenucleusisweI1knowntobesusceptibletomanyeletrophilicsubstitutionreactions2.Thereactionswithnucleophilicreagentsarealsoofinterest,sincechaIconesreactedwithhydroxylamine'andhydrazines'togiverespectivelydiary-substituteisoxazoIinesandpyrazolines.Thispaperdealswiththereactionsof3-acetyltropoloneand2-… 相似文献
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The starting substrate 3‐(3‐(1‐naphthyl)acryloyl)tropolone ( 3 ) was achieved by the aldol condensation reaction of 3‐acetyltropolone with 1‐naphthaldehyde. Compound 3 reacted with bromine to afford 7‐bromo‐3‐ (3‐(1‐naphthyl)acryloyl)tropolone ( 4 ), 5,7‐dibromo‐3‐(3‐(1‐naphthyl)acryloyl)tropolone (5) according to the molar ratio of the reactants. Iodination of 3 gave 7‐iodo‐3‐(3‐(1‐naphthyl)acryloyl)tropolone ( 6 ). Azo‐coupling reactions of 3 gave the 5‐arylazo‐3‐(3‐(1‐naphthyl)acryloyl)tropolones ( 7 – 8 ). Compounds 3 , 4 , 6 reacted respectively with hydroxyamine to give the corresponding 3‐[2‐(1‐naphthyl)vinyl]‐8H‐cyclohepta[d]isoxazol‐8‐ones ( 9 – 11 ). The reactions of 3 , 5 with phenylhydrazine and substituted phenylhydrazines gave 3‐[2‐(1‐naphthyl)vinyl]‐1‐phenylcyclohepta[c]pyrazol‐8(1H)‐ones ( 12 – 18 ). 相似文献
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以邻苯二胺及2,3-二氨基吡啶为原料,与羰基化合物反应制备苯并吡嗪、吡啶并吡嗪、苯并咪唑和吡啶并咪唑4种氮杂双环化合物,探讨了溶剂、温度、时间和pH值等实验条件对反应的影响。 在合成吡啶并吡嗪时,采用正丙醇为溶剂,用甲醇钠调节pH=9,回流反应1 h,将收率从35.7%提高至89.4%;在合成苯并吡嗪时,用水作溶剂,用亚硫酸钠调节pH=9,60 ℃反应40 min,产物纯化采用低温静置代替减压蒸馏,收率可提高至98.3%;尝试不同方法合成苯并咪唑和吡啶并咪唑,确定最优合成条件分别为:邻苯二胺在88%的甲酸溶液中回流2 h,苯并咪唑收率为92%;2,3-二氨基吡啶在原甲酸三已酯中回流3 h,加浓盐酸继续回流1 h,吡啶并咪唑收率为84.2%。 相似文献
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A convenient method to obtain a series of bromo‐substituted flavone‐like troponoid compounds 6,8‐dibromo‐2‐arylcyclohepta[b]pyran‐4,9‐diones 3a–3s by oxidation cyclization of the readily available intermediates 3‐cinnamoyl‐5,7‐dibromotropolones 2a–2s using I2/DMSO/H2SO4 system was realized. Compounds 2a–2s were obtained from the aldol reaction of 3‐acetyl‐5,7‐dibromotropolone 1 with various benzaldehydes. Compounds 2a–2s and 3a–3s are novel and their structures were supported by IR, 1H NMR, MS and elemental analyses. 相似文献
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T. K. Venkatachalam 《合成通讯》2013,43(20):3667-3675
Heterocyclic thioureas having multiple substitutions were prepared in two steps with overall yields of 60–80%. Condensation of a substituted heterocyclic amine with thiocarbonyldiimidazole, followed by treatment with a disubstituted phenylethylamine in dimethyl formamide (DMF), yielded the desired heterocyclic thioureas as crystalline solids. 相似文献
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通过3条路线合成得到8个新的2-取代嘧啶,2-噁(噻)1,3,4-噁噻二唑杂环化合物,其结构经1H NMR,EI-MS和元素分析表征. 相似文献