使用梅尔德鲁姆酸的克诺文纳格尔缩合/环化顺序反应

IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC
Shoko Yamazaki , Kohtaro Katayama , Yuta Mouri , Yuki Iwataki , Yuji Mikata , Tsumoru Morimoto
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引用次数: 0

摘要

研究人员利用环状活性亚甲基化合物(如梅尔德鲁姆酸)进行了顺序克诺文那格尔缩合/环化反应。在室温下,2-(1-苯基乙烯基)苯甲醛和梅尔杜姆酸、二美酮或 1,3-茚二酮与哌啶/AcOH 或 L-脯氨酸反应 17-18 小时,可得到环化茚衍生物,产率为 63-80%。2-(3,5-二甲氧基苯基)苯甲醛与 Meldrum's 酸在室温下反应 17 小时,可得到一种芴衍生物,收率为 98%。此外,2-(3,5-二甲氧基苄基)苯甲醛和梅氏酸与哌啶在室温下反应 18 小时后,生成了一种含梅氏酸的二氢蒽衍生物,收率为 83%。将 2-(3,5-二甲氧基苄基)苯甲醛和梅氏酸与哌啶在 110 °C 下反应 2 小时,可得到梅氏酸片段化的二氢蒽衍生物,收率为 48%。通过 DFT 计算研究了环化步骤和梅尔杜姆酸破碎的反应机理。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Sequential Knoevenagel condensation/cyclization reaction using Meldrum’s acid
Sequential Knoevenagel condensation/cyclization using cyclic active methylene compounds such as Meldrum’s acid have been studied. The reaction of 2-(1-phenylvinyl)benzaldehyde and Meldrum’s acid, dimedone, or 1,3-indandione with piperidine/AcOH or L-proline at room temperature for 17–18 h gave cyclized indene derivatives in 63–80% yield. The reaction of 2-(3,5-dimethoxyphenyl)benzaldehyde and Meldrum’s acid at room temperature for 17 h gave a fluorene derivative in 98% yield. Furthermore, the reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum’s acid with piperidine at room temperature for 18 h gave a dihydroanthracene derivative bearing Meldrum’s acid in 83% yield. The reaction of 2-(3,5-dimethoxybenzyl)benzaldehyde and Meldrum’s acid with piperidine at 110 °C for 2 h gave Meldrum’s acid fragmentated dihydroanthracene derivative in 48% yield. The reaction mechanisms of the cyclization steps and Meldrum’s acid fragmentation have been examined by the DFT calculations.
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来源期刊
Synthetic Communications
Synthetic Communications 化学-有机化学
CiteScore
4.40
自引率
4.80%
发文量
156
审稿时长
4.3 months
期刊介绍: Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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