以氨基氰为原料合成含氮化合物的研究进展

doi:10.6023/cjoc202208020

有机化学 ›› 2023, Vol. 43 ›› Issue (2): 436-454.DOI: 10.6023/cjoc202208020 上一篇下一篇

综述与进展

以氨基氰为原料合成含氮化合物的研究进展

吴江龙^†, 王中杰^†, 王晨宇, 王彦, 李红俊, 罗辉, 李昊, 王富强^*(), 李典军^*(), 杨金会^*()

宁夏大学化学化工学院/省部共建煤炭高效利用与绿色化工国家重点实验室银川 750021

收稿日期:2022-08-16 修回日期:2022-09-18 发布日期:2022-10-31
作者简介:
†共同第一作者
基金资助:
部委级自然科学其他项目(2019NXZD1); 宁夏自治区科技攻关(支撑)计划(2021BEG02001); 宁夏自治区科技攻关(支撑)计划(2021BEE03003); 及宁夏自治区重点研发计划(2022BDE03009)

Research Progress on the Synthesis of Nitrogen-Containing Compounds with Cyanamide as a Building Block

Jianglong Wu^†, Zhongjie Wang^†, Chenyu Wang, Yan Wang, Hongjun Li, Hui Luo, Hao Li, Fuqiang Wang(), Dianjun Li(), Jinhui Yang()

College of Chemistry and Chemical Engineering/State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, Ningxia University, Yinchuan 750021

Received:2022-08-16 Revised:2022-09-18 Published:2022-10-31
Contact: *E-mail: nxlidj@126.com;6960463@qq.com;yang_jh@nxu.edu.cn
About author:
†(These authors contributed equally to this work).
Supported by:
Ministry-Level Natural Science Other Projects(2019NXZD1); Scientific and Technological Research (Support) Project of Ningxia(2021BEG02001); Scientific and Technological Research (Support) Project of Ningxia(2021BEE03003); Key Research and Development Project of Ningxia(2022BDE03009)

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摘要/Abstract

含氮化合物存在于许多天然产物中, 具有广泛的药理和生理活性. 它们不仅被广泛应用于医药或农药领域, 在工业及多功能材料等领域也多有应用. 近年来, 含氮化合物的合成方法研究发展迅速, 不断有新的以氨基氰为原料合成各种含氮化合物的反应涌现. 简要介绍了近二十年来, 以氨基氰(NH₂-CN)作为原料合成各种含氮化合物的研究进展, 并归纳总结了它们的特点、规律和优劣势, 为它们的合成方法和反应性的研究提供帮助.

关键词: 氨基氰, 天然化合物, 含氮化合物, 药物分子

Nitrogen-containing compounds are widely found in many natural products and have a wide range of pharmaco- logical and physiological activities. Furthermore, they have comprehensive applications in medicine and pesticide fields, industry and multi-functional materials. Great advances in the synthesis of these compounds have been sprung up, a diversity of synthetic methods of them via cyanamide (NH₂-CN) as raw material were exploited in recent years. The research progress on the synthesis of nitrogen-containing compounds through cyanamide as a building block is introduced comprehensively. Moreover, their characteristics, rules, advantages and disadvantages are summarized and discussed for the development of new synthetic methodologies and reactions of nitrogen-containing compounds.

Key words: cyanamide, natural origin, nitrogen-containing compound, pharmaceutical

引用此文

吴江龙, 王中杰, 王晨宇, 王彦, 李红俊, 罗辉, 李昊, 王富强, 李典军, 杨金会. 以氨基氰为原料合成含氮化合物的研究进展[J]. 有机化学, 2023, 43(2): 436-454.

Jianglong Wu, Zhongjie Wang, Chenyu Wang, Yan Wang, Hongjun Li, Hui Luo, Hao Li, Fuqiang Wang, Dianjun Li, Jinhui Yang. Research Progress on the Synthesis of Nitrogen-Containing Compounds with Cyanamide as a Building Block[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 436-454.

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图/表 28

图1. 多种具有生物活性及药用价值的含氮杂环药物分子

Figure 1. A variety of nitrogen-containing heterocyclic drug molecules with biological activity and medicinal value

图式1. 胍中间体13的合成方法

Scheme 1. Desired transformation to guanidine intermediate 13

图式2. 钯催化羰基一锅法合成N-酰基胍

Scheme 2. Pd-catalyzed carbonylative one-pot synthesis of N-acylguanidines

图式3. 碘参与非金属条件下N-氰亚胺化合物的合成

Scheme 3. Iodinane and metal-free synthesis of N-cyano sulfilimines

图式4. 用氰胺和NBS进行醛的氰酰化反应

Scheme 4. Cyanoimidation of aldehydes using cyanamide and NBS

图式5. N-(1H)-四唑亚砜胺的合成

Scheme 5. Synthesis of N-(1H)-tetrazole sulfoximines

图式6. 以氨基氰为原料合成吡那地尔的路线

Scheme 6. Route to synthesize pinacidil using cyanamide as block

图式7. 铜催化氨基氰合成苯并咪唑并[2,1-b]喹唑啉-12(6H)-酮

Scheme 7. Copper-catalyzed synthesis of benzimidazo[2,1-b]quinazolin-12(6H)-ones from cyanamide

图式8. 铜催化2-溴-N-(2-溴苯基)苯甲酰胺和氨基氰反应合成苯并咪唑并[2,1-b]喹唑啉-12(6H)-酮

Scheme 8. Copper-catalyzed reaction of 2-bromo-N-(2-bromophenyl)benzamide and cyanamide for the synthesis of benzimidazo- [2,1-b]quinazolin-12(6H)-ones

图式9. 碱催化以氨基氰合成合成氨基烟腈

Scheme 9. Synthesis of aminonicotinonitriles through base-catalyzed with cyanamide

图式10. 由氨基氰合成氨基噁唑啉

Scheme 10. Synthesis of amino oxazoline from cyanamide

图式11. 乙烯基叠氮化物和氨基氰合成2-氨基咪唑

Scheme 11. Synthesis of polyfunctionalized 2-aminoimidazoles via vinyl azides and cyanamide

图式12. 氨基氰和α-硝基环氧化物开环制备2-氨基咪唑的策略

Scheme 12. Strategy for 2-aminoimidazoles via ring opening of α-nitro epoxides and and cyanamide

图2. 含有嘧啶骨架结构的药物分子

Figure 2. Drug molecules containing purine building block

图式13. 氨基氰、氰胺5-氨基吡唑-4-腈和原甲酸三乙酯一锅多组分合成4-氨基吡唑并三嗪腈类化合物

Scheme 13. A one-pot, three-component reaction of cyanamides, 5-aminopyrazole-4-carbonitriles and triethyl or thoformate for the synthesis of 4-aminopyrazolotriazine nitrile compounds

图3. 含有嘧啶骨架结构的药物分子

Figure 3. Drug molecules containing pyrimidine building block

图式14. 酸介导微波法使用氨基氰合成吡唑并嘧啶

Scheme 14. Acid catalytic microwave-assisted synthesis of pyrazolopyrimidines from cyanamide

图式15. 氨基氰合成吡唑并嘧啶可能的反应机理

Scheme 15. Proposed reaction mechanism of synthesis of pyrazolopyrimidine from cyanamide

图式16. 由腈合成取代嘧啶类化合物

Scheme 16. Synthesis of substituted pyrimidines from nitriles

图式17. 以氨基氰为原料合成抗抗真菌药物

Scheme 17. Route to synthesize antifungal drug using cyanamide as block

图式18. 氨基氰和二硫酯一锅法合成2-(杂)芳基/烷基噻唑类化合物

Scheme 18. A one-pot, reaction of cyanamides and dithioesters for the synthesis of 2-(hetero)aryl thiazoles compounds

图式19. 硝基苯胺和氨基氰合成苯并三嗪,

Scheme 19. Synthesis of benzotriazine from nitroaniline and cyanamine

图式20. 由氨基氰合成吖嗪衍生物

Scheme 20. Synthesis of acridine derivatives from cyanogen

图式21. 氨基氰、甲基酮和芳胺一锅多组分合成2-氨基-三嗪类化合物

Scheme 21. A one-pot, three-component reaction of cyanamides, methyl ketones and arylamines for the synthesis of 2-amino-triazines

图式22. 合成瑞德西韦核碱基的策略

Scheme 22. Strategies for synthesizing nucleobase of rindesivir

图式23. 以N-甲苯磺酰腙为导向合成1,2,4-三唑、1,3,4-噻二唑和1,3,4-硒二唑的方法

Scheme 23. Diversity-oriented synthesis of 1,2 4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones

图式24. 以氨基氰和N-甲苯磺酰腙合成1,2,4-三唑类化合物

Scheme 24. Synthesis of 1,2,4-triazole compounds from cyanamide and N-toluenesulfonyl hydrazone

图式25. 氨基氰与三氟甲基N-酰基腙的串联加成/环化合成3-三氟甲基-1,2,4-三唑啉

Scheme 25. Synthesis of 3-trifluoromethyl-1,2,4-triazolines via tandem addition/cyclization of trifluoromethyl N-acylhydrazones with cyanamide

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以氨基氰为原料合成含氮化合物的研究进展

Research Progress on the Synthesis of Nitrogen-Containing Compounds with Cyanamide as a Building Block

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