不同环化方式下吡咯合成的研究进展

doi:10.6023/cjoc202005018

有机化学 ›› 2021, Vol. 41 ›› Issue (1): 206-228.DOI: 10.6023/cjoc202005018 上一篇下一篇

综述与进展

不同环化方式下吡咯合成的研究进展

徐学涛^a, 陈洁^a, 柯俊杰^a, 张焜^a, 吴盼盼^a^,^*(), 王少华^b^,^*()

a 五邑大学生物科技与大健康学院广东江门 529020
b 兰州大学药学院兰州 730000

收稿日期:2020-05-08 修回日期:2020-07-15 发布日期:2020-08-01
通讯作者: 吴盼盼, 王少华
作者简介:
* Corresponding authors. E-mail: wyuchemwpp@126.com; wangshh@lzu.edu.cn
基金资助:
国家自然科学基金(21472077); 国家自然科学基金(21772071); 中央高校基本科研基金(lzujbky-2018-134); 广东省教育厅(2017KTSCX185); 广东省教育厅(2017KSYS010); 广东省教育厅(2020KCXTD036); 广东省教育厅(2019KZDXM035)

Recent Advances on Pyrrole Synthesis through Different Annulation Modes

Xuetao Xu^a, Jie Chen^a, Junjie Ke^a, Kun Zhang^a, Panpan Wu^a^,^*(), Shaohua Wang^b^,^*()

a School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020
b School of Pharmacy, Lanzhou University, Lanzhou 730000

Received:2020-05-08 Revised:2020-07-15 Published:2020-08-01
Contact: Panpan Wu, Shaohua Wang
Supported by:
the National Natural Science Foundation of China(21472077); the National Natural Science Foundation of China(21772071); the Fundamental Research Funds for the Central Universities(lzujbky-2018-134); the Department of Education of Guangdong Province(2017KTSCX185); the Department of Education of Guangdong Province(2017KSYS010); the Department of Education of Guangdong Province(2020KCXTD036); the Department of Education of Guangdong Province(2019KZDXM035)

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摘要/Abstract

吡咯作为一种重要的杂环, 广泛存在于天然产物、人造活性成分和功能材料等各种功能分子中. 这一事实促进了这种结构单元合成方法学的发展. 总结了近五年来不同环化方式下吡咯合成的研究进展.

关键词: 吡咯, 环化方式, 合成, 研究进展

Pyrrole, as one of the most important heterocycles, broadly exists in various functional molecules ranging from biological contexts to natural products, man-made bioactive molecules and functional materials. Such a fact has prompted the methodology development toward the construction of such a structural unit. The recent advances on pyrrole synthesis are summarized based on different cyclization modes.

Key words: pyrrole, cyclization modes, synthesis, recent advance

引用此文

徐学涛, 陈洁, 柯俊杰, 张焜, 吴盼盼, 王少华. 不同环化方式下吡咯合成的研究进展[J]. 有机化学, 2021, 41(1): 206-228.

Xuetao Xu, Jie Chen, Junjie Ke, Kun Zhang, Panpan Wu, Shaohua Wang. Recent Advances on Pyrrole Synthesis through Different Annulation Modes[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 206-228.

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图/表 97

Figure 1. Structures of chlorophylls, hemes and coenzyme F430

Figure 2. Selected bioactive natural products with pyrrole skeleton

Figure 3. Some representative natural products isolated during the past five years

Figure 4. Selected pyrrole containing clinic drugs

Scheme 1. Fe(II)-catalyzed ring isomerization

Scheme 2. Ring contraction of 3,6-dihydro-1,2-oxazines

Scheme 3. PdCl2 mediated tandem heteropalladation/isocya- nate insertion reaction

Scheme 4. Cyclization of homopropargylamines and sulfinic acids

Scheme 5. Iridium-catalyzed fragmentation/cyclization cascade

Scheme 6. Au-catalyzed cyclization of enyne sulfonamides

Scheme 7. Au-promoted cyclization ofN-propargyl-N-vinyl sulphonamides

Scheme 8. Silver or cesium catalyzed reaction of trifluoromethyl-substituted 3-aza-1,5-enynes

Scheme 9. tBuOK-promoted annulation of N-propargylic β- enaminones

Scheme 10. KOH-catalyzed cyclization ofN-propargylicβ- enaminones

Scheme 11. tBuOK-mediated reaction ofN-propargylβ-ena- minones

Scheme 12. Nickel-catalyzed cyclization ofN-tosylalkyn-amide

Scheme 13. Gold-catalyzed tandem cyclization reaction

Scheme 14. Organocatalytic cycloisomerization ofZ-1-iodo- 4-N-methylbenzenesulfonyl-1,6-enynes

Scheme 15. Palladium-promoted cyclization of 1-(1-alkynyl)- cyclopropyl oximes

Scheme 16. Copper-catalyzed cyclization of propargylα-imi- nodiazoacetates

Scheme 17. Aluminum-promoted cyclization of tertiary enamides

Scheme 18. Molybdenum-catalyzed annulation of nitrodienes

Scheme 19. Cobalt pincer complexes promoted synthesis of pyrroles

Scheme 20. Nickel-mediated pyrrole synthesis via a formal [4+1] cyclization

Scheme 21. Au-catalyzed rearrangement/cyclization cascade

Scheme 22. One pot sequence between 2-furylcarbinols and anilines for pyrrole construction

Scheme 23. Zinc-mediated cyclization process between 1,2- cyclopropanated sugars and amines

Scheme 24. Oxalic acid promoted reaction of carbohydrates and primary amines

Scheme 25. Copper-catalyzed cyclization between 1,3-enynes with aromatic amines

Scheme 26. Gold-catalyzed cyclization of benzyl azides and 3-en-1-ynamides

Scheme 27. Gold-catalyzed cyclization of 1,4-diyn-3-ols withN-hydroxyanilines

Scheme 28. Gold-promoted reaction of 1,4-diyn-3-ols and isoxazoles

Scheme 29. Gold-catalyzed cyclization between 4-methoxy- 1,2-dienyl-5-ynes and anthranils

Scheme 30. Rhodium and silver-catalyzed reaction of allylamines and alkenes

Scheme 31. Copper catalyzed annulation of propargylamines

Scheme 32.

. Palladium-promoted pyrrole synthesis betweenα-tosylamideallenes and alkynes

Scheme 33. Palladium-catalyzed reaction of imines, aryl iodides and CO

Scheme 34.

. Cycloaddition reaction of sulfurylides andα,β- unsaturated imines

Scheme 35. Gold-promoted cyclization of isoxazoles and propiolate

Scheme 36. Fe-promoted cyclization reaction between methylene ketones and diethanolamines

Scheme 37.

. Pt/C-catalyzed annulation of secondary alcohols and 1,2-amino alcohols

Scheme 38.

. Manganese-catalyzed pyrrole synthesis from alcohols and amino alcohols

Scheme 39. Gold-catalyzed cyclization of α-amino ketones and alkynes

Scheme 40.

. Lewis base-catalyzed cyclization protocol of 2- aminoketones withβ'-acetoxyallenoate

Scheme 41.

. Copper-catalyzed cycloaddition of propargylic esters withβ-enamino esters

Scheme 42.

. Cu(II)-promoted annulation ofα-enamino esters and activated alkynes

Scheme 43. Cobalt-catalyzed cycloaddition of enamides and alkynes

Scheme 44. I2-catalyzed reaction between enamines and allenes

Scheme 45. I2-catalyzed annulations ofβ-nitrostyrene

Scheme 46. K3PO4-catalyzed cyclization between propargyl amines and activated alkynes

Scheme 47. Rhodium-promoted annulation of propargylamines and ethyl vinyl ether

Scheme 48.

. Copper-catalyzed three component reaction for pyrrole synthesis

Scheme 49. DBU-promoted annulation of ynones andN-sub- stituted ethyl glycine ethyl ester

Scheme 50. Silver-catalyzed cyclization of isocyanides and chromones

Scheme 51.

. Cyclization between methyl isocyanoacetate and aurone analogues

Scheme 52.

. Copper-catalyzed alkyne-isocyanide cycloaddition/ring expansion reaction

Scheme 53. Copper-catalyzed cyclization of ethyl allenoates and activated isocyanides

Scheme 54. PPh3-promoted cyclization of allenoates with activated isocyanides

Scheme 55. Silver-catalyzed reaction ofβ-enaminones and isocyanoacetates

Scheme 56. Tandem cyclization of isocyanides and 2-iso- cyanochalcones

Scheme 57.

. Yb(OTf)3 and Ag2CO3-catalyzed cyclization of enynones and isocyanides

Scheme 58.

. Gold-catalyzed annulation between isoxazoles and ynamides

Scheme 59. Gold-catalyzed cycloaddition between ynamides and isoxazoles

Scheme 60. One-pot pyrrole synthesis from 5-methoxy- isoxazoles and pyridiniumylides

Scheme 61. Photo induced cobalt-catalyzed cyclization of isoxazoles and acetylacetone

Scheme 62.

. Iridium-catalyzed cycloaddition between 2,3-dihy- droisoxazoles and chalcones

Scheme 63. Amine catalyzed cyclization between Mu?nchnones and enamines

Scheme 64.

. Rhodium-catalyzed cycloaddition of 2H-azirines withN-sulfonyl-1,2,3-triazoles

Scheme 65. Copper-catalyzed annulation between ketones and vinyl azides

Scheme 66.

. Gold-catalyzed cycloadditions between ynamides and vinyl azides or 2H-azirines

Scheme 67.

. Fe(II)-catalyzed cycloaddition of 2H-azirines and enamides

Scheme 68. Cesium-promoted reaction of alkyl 2-aroyl-1- chlorocyclopropanecarboxylates and acylhydrazono esters

Scheme 69.

. Reaction of donor-acceptor cyclopropanes, salicylaldehydes and ammonium acetate

Scheme 70.

. Copper-catalyzed cyclization between ketimines andα-diazo-β-ketoesters

Scheme 71. LDA-promoted annulation between alkynyl Fischer carbenes withα-imino glycine methyl esters

Scheme 72. Rh-catalyzed annulation betweenα-diazo oxime with vinyl equivalents

Scheme 73.

. Cyclization of arylidenmalononitrile, malononitrile and hydroxylamine hydrochloride

Scheme 74. Copper-catalyzed reaction betweenα-acidic isocyanides and nitrone

Scheme 75.

. Bezoic acid-promoted annulation of 2,3-dike- toesters, ketones and amines

Scheme 76.

. Cyclization of 1,2-diarylethan-1-ones and benzoins

Scheme 77. Electrooxidative annulation between amines and aldehydes or ketones

Scheme 78.

. Copper-catalyzed annulation of alkylamines and aromatic acetaldehydes

Scheme 79.

. [Cu(NHC)]-catalyzed cyclization of ketone, primary amine and diol

Scheme 80.

. Manganese-catalyzed cyclization of ketones, amine, and diols

Scheme 81. Brønsted acid catalyzed annulation of silylenolates and primary amines

Scheme 82. Copper/manganese co-catalyzed reaction between styrenes, acetone and arylamines Besides carbonyl type of compound, alkenes or alkynes are also used as the C2 units for pyrrole synthesis via [2+ 2+1] mode.

Scheme 83.

. Ti-catalyzed cyclization between alkynes and diazenes

Scheme 84.

. Ti-catalyzed annulation of alkynes with phenyl diazene

Scheme 85.

. Ti(II)/Ti(IV) redox-promoted reaction between azides and alkynes

Scheme 86. Pd(II)-promoted cyclization of amines, alkyne esters, and alkenes

Scheme 87. Cyclization of primary amine,α-nitroepoxide and dialkyl acetylenedicarboxylate

Scheme 88. K2CO3-mediated annulation ofα-nitro epoxides, amines and malononitrile

Scheme 89. Zirconocene dichloride-catalyzed cyclization of amines, nitroalkenes, andβ-dicarbonyl compounds

Scheme 90. Cyclization of alkylnitriles, arylalkynes and MeOTf

Scheme 91. Palladium-promoted cyclization between propargylic carbonates and isocyanides

Scheme 92. Pd-catalyzed reactions of propargyl carbonates, isocyanides, and alcohols or water

Scheme 93.

. Palladium-promoted annulation of aryl halides,N-tosylhydrazones, and isocyanides

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不同环化方式下吡咯合成的研究进展

Recent Advances on Pyrrole Synthesis through Different Annulation Modes

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