M(OTf)_3 Catalyzed Novel Mannich Reaction of N- Alkyoxycarbonylpyrrole or Thiophene, Formaldehyde and Primary Amine Hydrochloride

Acta Chimica Sinica ›› 2002, Vol. 60 ›› Issue (3): 481-486. Previous Articles Next Articles

Original Articles

M(OTf)_3催化N－烷氧羰基吡咯或噻吩醛和盐酸伯胺的新颖Mannich反应

张传新;程铁明;李润涛

北京大学院.北京(100083)

发布日期:2002-03-15

M(OTf)_3 Catalyzed Novel Mannich Reaction of N- Alkyoxycarbonylpyrrole or Thiophene, Formaldehyde and Primary Amine Hydrochloride

Zhang Chuanxin;Cheng Tieming;Li Runtao

School of Pharmaceutical Sciences, Peking University.Beijing(100083)

Published:2002-03-15

Abstract

A novel Mannich reaction between N-Alkoxycarbonylpyrrole, formaldehyde and primary amine hydrochlorides is catalyzed by M(OTf)_3 (M = Sc, Y, Ln) in aqueous media. Among three catalysts, Y(OTf)_3 is the best. The products are obtained in good yields under mild conditions. This method can be used for thiophene. This is an atom- economic reaction and meets the requirements of green chemistry.

Key words: MANNICH REACTION, SULFONATE, PYRROLE, THIOPHENE, MANNICH BASE

CLC Number:

O621

Cite this article

Zhang Chuanxin;Cheng Tieming;Li Runtao. M(OTf)_3 Catalyzed Novel Mannich Reaction of N- Alkyoxycarbonylpyrrole or Thiophene, Formaldehyde and Primary Amine Hydrochloride[J]. Acta Chimica Sinica, 2002, 60(3): 481-486.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Yanqin Huang, Lijun Li, Shupei Yang, Rui Zhang, Xingfen Liu, Quli Fan, Wei Huang. HA-AuNPs/FDF for Highly Sensitive Detection of Hyaluronidase, Tumor-targeting Fluorescence Cell Imaging and Phototherapy [J]. Acta Chimica Sinica, 2023, 81(12): 1687-1694.
[2]	Yang Wang, Junjun Xiang, Congwu Ge, Xike Gao. Study on Main Chain Structure Regulation and Properties of Conjugated Copolymers Based on 2,6-Azulene and 3,4-Propylenedioxythiophene^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1341-1349.
[3]	Jie Zhao, Zhiwen Wang, Huaqing Li, Qi Ai, Peiqing Cai, Junjie Si, Xin Yao, Xiaoguang Hu, Zugang Liu. Synthesis and Properties of Visible-light-driven Fluorescence Turn-on Diarylethenes Based on Benzo[b]naphtho[1,2-d]thiophene [J]. Acta Chimica Sinica, 2022, 80(9): 1223-1230.
[4]	Xinming Hu, Chunxiao Zhong, Xiaoyan Li, Xiong Jia, Ying Wei, Linghai Xie. Synthesis and Application of Cyclopentadithiophene Derivatives [J]. Acta Chimica Sinica, 2021, 79(8): 953-966.
[5]	Bo Zhou, Renxiao Liang, Zhongyan Cao, Pinghai Zhou, Yixia Jia. Palladium-Catalyzed Heck Reaction of Endocyclic Conjugated C=C Bonds of Pyrroles [J]. Acta Chimica Sinica, 2021, 79(2): 176-179.
[6]	Gao Simeng, Xia Kun, Kang Zhihong, Nai Yongning, Yuan Ruixia, Niu Ruixia. Molecular Dynamics Simulation of “Quasi-Gemini” Anionic Surfactant at the Decane/Water Interface [J]. Acta Chimica Sinica, 2020, 78(2): 155-160.
[7]	Yang, Junhang, Fu, Xiaobo, Lu, Zenghui, Zhu, Gangguo. Visible-Light Photocatalytic Remote Thiolation of Aldehydes Triggered by Sulfonylation of Alkenes With Thiosulfonates [J]. Acta Chimica Sinica, 2019, 77(9): 901-905.
[8]	Luo Jianxin, Yan Wenhai, Ma Qing, Zhang Chunyan, Fang Yiquan, Zhang Xucheng, Wang Changchun. Study on High Activity Monodispersed Sulfonated Porous Polystyrene Microspheres for Preparation of Biodiesel [J]. Acta Chimica Sinica, 2019, 77(1): 54-59.
[9]	Cui Huina, Qiu Feng, Peng Juan. Synthesis and Properties of an All-Conjugated Polythio-phene-Polyselenophene Diblock Copolymer [J]. Acta Chim. Sinica, 2018, 76(9): 691-700.
[10]	He Yuanyuan, Cheng Na, Zhao Jianwei. Electron Transport Pathways Through One-Dimensional Conjugated Carbon Chain Doped by Thiophene Ring [J]. Acta Chim. Sinica, 2017, 75(9): 893-902.
[11]	Shi Minglin, Zhan Gu, Du Wei, Chen Yingchun. Direct Asymmetric Aza-Vinylogous Mannich Reaction of Nitrones from Isatins and Ketimines [J]. Acta Chim. Sinica, 2017, 75(10): 998-1002.
[12]	Zhu Haoyun, Huang Wei, Huang Yuli, Wang Weizhi. Field Effect Transistors Characteristics Based on Blends of Si Nanowires and Poly(3-dodecylthiophene) [J]. Acta Chim. Sinica, 2016, 74(5): 429-434.
[13]	Zhao Caibin, Wang Zhanling, Zhou Ke, Ge Hongguang, Zhang Qiang, Jin Lingxia, Wang Wenliang, Yin Shiwei. Theoretical Investigation on Photovoltaic Properties of BDT and DPP Copolymer as a Promising Organic Solar Cell [J]. Acta Chim. Sinica, 2016, 74(3): 251-258.
[14]	Peng Zhe, Ji Yingchun, Wang Zhi, Tong Bin, Shi Jianbing, Dong Yuping. Properties of Polymorphism and Acid Response of Pyrrolopyrrole-based Derivative with Aggregation-induced Emission Behavior [J]. Acta Chim. Sinica, 2016, 74(11): 942-948.
[15]	Li Xin-Ling, Wang Jia-Qi, Li Long, Yin Ying-Wu, Ye Long-Wu. Facile Synthesis of 2H-Pyrroles: Combination of Gold Catalysis and Lewis Acid Catalysis [J]. Acta Chim. Sinica, 2016, 74(1): 49-53.

M(OTf)_3催化N－烷氧羰基吡咯或噻吩醛和盐酸伯胺的新颖Mannich反应

M(OTf)_3 Catalyzed Novel Mannich Reaction of N- Alkyoxycarbonylpyrrole or Thiophene, Formaldehyde and Primary Amine Hydrochloride

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments