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有机化学
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有机化学 ›› 2020, Vol. 40 ›› Issue (8): 2526-2530.DOI: 10.6023/cjoc202004004 上一篇    下一篇

研究简报

N-氯代丁二酰亚胺促进下萘醌并呋喃衍生物的高效合成

王翔, 陈平, 支三军, 胡华友, 阚玉和, 张载超   

  1. 淮阴师范学院化学化工学院 江苏省低维材料化学重点实验室 江苏淮安 223300
  • 收稿日期:2020-04-02 修回日期:2020-05-12 发布日期:2020-06-01
  • 通讯作者: 王翔, 张载超 E-mail:hurricanwx@163.com;zhangzc@hytc.edu.cn
  • 基金资助:
    国家自然科学基金（Nos.21601061，51403073）、江苏省高等学校自然科学研究（No.16KJB150006）、江苏省低维材料化学重点实验室开放基金（No.JSKC15145）资助项目.

N-Chloro-succinimide-Promoted Efficient Synthesis of Naphthofuran-4,9-dione Derivatives

Wang Xiang, Chen Ping, Zhi Sanjun, Hu Huayou, Kan Yuhe, Zhang Zaichao   

  1. Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai'an, Jiangsu 223300
  • Received:2020-04-02 Revised:2020-05-12 Published:2020-06-01
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21601061, 51403073), the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (No. 16KJB150006), the Jiangsu Key Laboratory for Chemistry of Low-Dimensional Materials (No. JSKC15145).

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补充材料

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萘醌并呋喃类化合物具有广谱的生理和药理活性，为该类化合物提供绿色高效的合成方法具有重要意义.报道了2-氨基-3-氰基萘醌并吡喃以及2-氨基-3-甲酸乙酯基香豆素并吡喃衍生物和醇的串联反应，在N-氯代丁二酰亚胺（NCS）促进下，于室温条件下反应30 min，以48%~97%的产率得到目标产物.反应经过开环、再环化过程，生成了两类结构新颖的稠合呋喃类化合物.

关键词: 萘醌并呋喃, N-氯代丁二酰亚胺, 串联反应, 杂环

Naphthofuran-4,9-dione derivatives exhibit a broad spectrum of biological and medicinal activities. The development of green and efficient methods for the synthesis of these heterocyclic compounds is of great importance. In this paper, the N-chloro-succinimide (NCS)-promoted reaction of 2-amino-benzo[g]chromene-3-carbonitriles or ethyl 2-amino-pyrano[3,2-c]-chromene-3-carboxylates with alcohols lead to the naphthofuran-4,9-dione or diethyl furo[3,2-c]chromene-2,2-dicarboxylate was reported. All reactions were completed in 30 min under room temperature, and two types of novel fused furan derivatives were obtained in 48%~97% yields under tandem ring-opening/cyclization processes.

Key words: naphthofuran-4,9-dione, NCS, domino reaction, heterocyclic