Recent Advances on Pyrrole Synthesis through Different Annulation Modes

doi:10.6023/cjoc202005018

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 206-228.DOI: 10.6023/cjoc202005018 Previous Articles Next Articles

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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)

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

Cite this article

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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Fig. & Tab. 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 3. PdCl2 mediated tandem heteropalladation/isocya- nate insertion reaction

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 13. Gold-catalyzed tandem cyclization reaction

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

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

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

. Palladium-promoted pyrrole synthesis betweenα-tosylamideallenes and alkynes

. Cycloaddition reaction of sulfurylides andα,β- unsaturated imines

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

. Manganese-catalyzed pyrrole synthesis from alcohols and amino alcohols

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

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

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

Scheme 44. I2-catalyzed reaction between enamines and allenes

. Copper-catalyzed three component reaction for pyrrole synthesis

. Cyclization between methyl isocyanoacetate and aurone analogues

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

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

. Gold-catalyzed annulation between isoxazoles and ynamides

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

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

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

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

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

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

. Cyclization of arylidenmalononitrile, malononitrile and hydroxylamine hydrochloride

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

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

. Copper-catalyzed annulation of alkylamines and aromatic acetaldehydes

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

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

. Ti-catalyzed cyclization between alkynes and diazenes

. Ti-catalyzed annulation of alkynes with phenyl diazene

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

. 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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