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2022 , Vol. 42 >Issue 11: 3704 - 3713

DOI: https://doi.org/10.6023/cjoc202204033

研究论文

1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)驱动的双分子硝基烷烃对重氮化合物的亲核加成反应: 多官能化腙和四氢哒嗪化合物的合成

  • 张骁勇 ,
  • 于丽丽 ,
  • 高俊芳 ,
  • 宫岳 ,
  • 赵玉龙
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  • a包头师范学院化学学院 内蒙古包头 014030
    b东北师范大学化学学院 吉林省有机功能分子设计与合成重点实验室 长春 130024

收稿日期: 2022-04-13

  修回日期: 2022-07-24

  网络出版日期: 2022-08-10

基金资助

国家自然科学基金(21871044); 国家自然科学基金(22165022)

收起

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Nucleophilic Addition of Two Molecules of Nitroalkanes to Diazo Compounds: Synthesis of Highly Functionalized Hydrazones and Tetrahydropyridazines

  • Xiaoyong Zhang ,
  • Lili Yu ,
  • Junfang Gao ,
  • Yue Gong ,
  • Yulong Zhao
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  • aDepartment of Chemistry, Baotou Teachers’ College, Baotou, Inner Mongolia 014030
    bJilin Provincial Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University, Changchun 130024
*E-mail:

Received date: 2022-04-13

  Revised date: 2022-07-24

  Online published: 2022-08-10

Supported by

National Natural Sciences Foundation of China(21871044); National Natural Sciences Foundation of China(22165022)

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摘要

以重氮化合物作为有效的端氮亲电试剂, 成功实现了1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)驱动的两分子硝基烷烃对重氮化合物分子间的亲核加成反应. 该反应从易得的起始原料出发, 提供了两种在温和反应条件下一步构建含有硝基烷烃基本结构单元的官能化腙和四氢哒嗪类化合物的新方法. 该反应涉及连续的分子间亲核加成/消除/分子间Aza-Henry反应/分子内环化反应过程, 一步产生两个或三个相邻的立体中心.

关键词： 重氮化合物; 端氮亲电试剂; 硝基烷烃; 腙; 四氢哒嗪

本文引用格式

张骁勇 , 于丽丽 , 高俊芳 , 宫岳 , 赵玉龙 . 1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)驱动的双分子硝基烷烃对重氮化合物的亲核加成反应: 多官能化腙和四氢哒嗪化合物的合成[J]. 有机化学, 2022 , 42(11) : 3704 -3713 . DOI: 10.6023/cjoc202204033

Abstract

A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted intermolecular addition reaction two molecules of nitroalkanes to diazo compounds has been developed, in which diazo compounds sereve as the efficient N-terminal electrophiles. The reaction provides two new and highly efficient methods for the construction of functionalized hydrazones and tetrahydropyridazines bearing the structure feature of nitroalkanes from readily available starting materials. The reaction involves a sequential intermolecular nucleophilic addition/elimination/intermolecular Aza-Henry reaction/intramolecular cyclization procedure where two or three adjacent stereocenters are created simultaneously in one-pot manner.

Key words： diazo compound; N-terminal electrophile; nitroalkane; hydrazone; tetrahydropyridazine

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