N—N键合成方法的研究进展

doi:10.6023/cjoc202111019

摘要/Abstract

N—N键广泛存在于药物、天然产物和有机功能材料中, 如何高效构建N—N键是有机合成的一个重要研究方向. 基于含氨基、氰基、硝基和叠氮基等含氮基团的有机化合物非常多, 直接利用这些含氮基团进行N—N键偶联为合成含N—N键结构单元的有机化合物提供了新的策略. 综述了近年来发展的分子间和分子内构建N—N键的合成方法, 并且对该方法存在的难点以及未来发展方向进行了展望.

关键词: N-N偶联, 含氮基团, 氮杂环, N—N键

Nitrogen-nitrogen bonds are widely found in drugs, nature products and organic materials. Design and synthesis of nitrogen-nitrogen motifs with high efficiency have always been an important issue in organic chemistry. The nitrogen sources such as amines, nitriles, nitroso, and azides or other N-functionalized reagents, are commonly exist in organic compounds. Direct N-N coupling of these nitrogen sources provides a more convergent synthesis strategy to produce different heterocycles and hydrazines containing the N-N motif. In this paper, the intermolecular and intramolecular formation of N—N bond in recent years is reviewed, and the difficulties and future development of this method are prospected.

Key words: N-N coupling, N-containing group, N-heterocycle, N—N bond

引用此文

赵伟哲, 许佳栗, 杨帆, 曾祥华. N—N键合成方法的研究进展[J]. 有机化学, 2022, 42(5): 1336-1345.

Weizhe Zhao, Jiali Xu, Fan Yang, Xianghua Zeng. Advances on the Synthesis of N—N Bonds[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1336-1345.

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图/表 29

图1. 含N—N键结构的分子

Figure 1. Molecules containing N—N bond

图2. 构建N—N键的方法

Figure 2. Methods for construction of N—N bond

图式1. 二芳香胺的去氢偶联

Scheme 1. Dehydrogenative coupling of diarylamines

图式2. 咔唑的去氢偶联

Scheme 2. Dehydrogenative coupling of carbazoles

图式3. 仲胺的去氢偶联

Scheme 3. Dehydrogenative coupling of secondary amines

图式4. 氮宾促进分子间的N—N键偶联

Scheme 4. Nitrene-mediated intermolecular N—N coupling

图式5. 碘或膦促进分子间的N—N键偶联

Scheme 5. Iodine or phospine-mediated intermolecular N—N coupling

图式6. 铜催化合成三唑

Scheme 6. Copper-catalyzed synthesis of triazoles

图式7. 铜或碱促进三唑的合成

Scheme 7. Copper or base-mediated synthesis of triazoles

图式8. 铜促进四取代吡唑的合成

Scheme 8. Copper-mediated synthesis of tetrasubstituted pyrazoles

图式9. 钛催化促进四取代吡唑的合成

Scheme 9. Ti-catalyzed synthesis of tetrasubstituted pyrazoles

图式10. 铜催化吡唑并[1,5-a]吲哚衍生物的合成

Scheme 10. Cu-catalyzed synthesis of pyrazolo[1,5-a]indole derivatives

图式11. 钯催化吡啶并[1,2-b]吲唑的合成

Scheme 11. Pd-catalyzed synthesis of pyrido[1,2-b]indazoles

图式12. 合成1H-吲唑的方法

Scheme 12. Methods for the synthesis of 1H-indazoles

图式13. 碱促进2H-吲唑的合成

Scheme 13. Base-mediated synthesis of 2H-indazoles

图式14. 合成四嗪衍生物

Scheme 14. Synthesis of tetrazine derivatives

图式15. 光催化丙啶的合成

Scheme 15. Photocatalytic synthesis of diaziridines

图式16. 无催化剂条件下合成1,2,3-三氮唑

Scheme 16. Catalyst-free synthesis of 1,2,3-triazoles

图式17. 吲唑酮的合成方法

Scheme 17. Methods for synthesis of indazolone derivatives

图式18. 2H-吲唑的合成方法

Scheme 18. Methods for synthesis of 2H-indazoles

图式19. 吡啶并[1,2-b]吲唑的合成方法

Scheme 19. Methods for synthesis of pyrido[1,2-b]indazoles

图式20. 铜催化1H-吲唑的合成

Scheme 20. Cu-catalyzed synthesis of 1H-indazoles

图式21. 钨酸钠催化1H-吲唑的合成

Scheme 21. Na2WO4-catalyzed synthesis of 1H-indazoles

图式22. 1H-吡唑的合成方法

Scheme 22. Methods for synthesis of 1H-pyrazoles

图式23. 吡唑-5酮的合成方法

Scheme 23. Methods for synthesis of pyrazolin-5-ones

图式24. 吡唑啉的合成方法

Scheme 24. Methods for synthesis of pyrazolines

图式25. 三唑并吡啶的合成方法

Scheme 25. Methods for synthesis of triazolopyridines

图式26. 噌啉和哒嗪-1,4-二酮的合成方法

Scheme 26. Methods for synthesis of cinnolines and phthalazin-1,4-diones

图式27. 哒嗪的合成方法

Scheme 27. Methods for synthesis of pyridazines

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