Synthesis of some berbine derivatives with nitro group in ring D via photocyclization

Abstract

Six berbine derivatives 2f~2k with nitro group in ring D have been synthesized via photocyclization 2-methoxy-nitro-benzoyl chlorides reacted with 1-methyl-6,7-dimethoxy (or 6-methoxy-7-benzyloxy)-3,4- dihydro-isoquinolines to give 1-methylene-6,7-dimethoxy (or 6-methoxy- 7-benzyloxy)-N-(2'-methoxy-nitro-benzoyl)-1,2,3,4-tetrahydro- isoquinolines (3) along with unexpected by-products whose structures were identified as 1-methyl-1-(2'-methoxy-benzoyl)-6,7-dimethoxy (or 6-methoxy-7-benzyloxy)-1,2,3,4-tetrahydro-isoquinolines (5). Irradiation of compounds 3 in methanol gave 2,3-dimethoxy (or 2- benzyloxy-3-methoxy) 8-oxo-13,13a-didehydro-berbines (4) with nitro group in ring D and a small amount of corresponding 5. Compounds 4 were treated with POCl3 followed by NaBH4 to afford the berbine derivatives 2f~2k.

Key words: ALKALOID, INFRARED SPECTROPHOTOMETRY, MASS SPECTROGRAPHY, CYCLIZATION, PROTON MAGNETIC RESONANCE SPECTROMETRY

CLC Number:

R914

Cite this article

YE ZHENGOU;ZHOU QITING. Synthesis of some berbine derivatives with nitro group in ring D via photocyclization[J]. Acta Chimica Sinica, 1997, 55(2): 202-208.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Wang Rui-Xiang, Zhao Qing-Ru, Gu Qing, You Shu-Li. Gold/Iridium Catalyzed Alkynylamide Cyclization/Asymmetric Allylic Benzylation Cascade Reaction^★ [J]. Acta Chimica Sinica, 2023, 81(5): 431-434.
[2]	Huang Jiapian, Liu Fei, Wu Jie. Recent Advances in the Transformation of Difluorocyclopropenes^★ [J]. Acta Chimica Sinica, 2023, 81(5): 520-532.
[3]	Lai Zhang, Jian Xiao, Yawen Wang, Yu Peng. Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes [J]. Acta Chimica Sinica, 2022, 80(8): 1152-1164.
[4]	Jiang Chongguo, Chen Sijia, Gong Jianxian, Yang Zhen. Synthetic Study Toward the 4,5-Spirocycle Skeleton of Phainanoids [J]. Acta Chimica Sinica, 2020, 78(9): 928-932.
[5]	Jia Xiaoyan, Li Zhenhuan. Synthesis of N-Carboxy Alanine Anhydride from Alanine and Dimethyl Carbonate over NaZnPO₄ in One-pot [J]. Acta Chimica Sinica, 2020, 78(6): 540-546.
[6]	Qian, Xiangyang, Xiong, Peng, Xu, Hai-Chao. Modular Synthesis of Functionalized 4-Quinolones via a Radical Cyclization Cascade Reaction [J]. Acta Chimica Sinica, 2019, 77(9): 879-883.
[7]	Xu, Jian, Zhang, Shifan, Luo, Ying, Zhang, Li, Zhang, Fan, Huang, Tingjing, Song, Qiuling. Radical Promoted Annulation of Alkynones for the Construction of 2,3-Disubstituted Thiochromones [J]. Acta Chimica Sinica, 2019, 77(9): 932-938.
[8]	Yang Zhongbo, Li Sujia, Luo Sanzhong. Total Synthesis of (±)-Hongoquercin A via Visible-Light-Mediated Organocatalytic Polyene Cyclization [J]. Acta Chim. Sinica, 2017, 75(4): 351-354.
[9]	Yu Kuan, Gao Beiling, Ding Hanfeng. Asymmetric Total Synthesis and Absolute Configuration Reassignment of Indole Alkaloid (+)-Alsmaphorazine D [J]. Acta Chim. Sinica, 2016, 74(5): 410-414.
[10]	Jian-Feng Zheng, Zhi-Qiang Xie, Xin-Jian Chen, Pei-Qiang Huang. Direct Transformation of Amides: Reductive Cycloaddition of Secondary Amides with Danishefsky Diene [J]. Acta Chim. Sinica, 2015, 73(7): 705-715.
[11]	Cai Zhongjian, Lu Xinmou, Wang Shunyi, Ji Shunjun. Copper-Catalyzed Cyclization of Oxime Acetates with 2-Benzylidenemalononitriles for Synthesis of 2?Aminonicotinonitriles [J]. Acta Chimica Sinica, 2014, 72(8): 914-919.
[12]	Hu Ludan, Gao Lingfeng, Wan Changfeng, Wang Zhiyong. A Practical Iodine-Catalyzed Sequential Process：Assembly of Imidazo[1,5-a]pyridines From Aldehydes [J]. Acta Chimica Sinica, 2013, 71(12): 1603-1606.
[13]	Zhang Baiqun, Wan Changfeng, Wang Qiang, Zhang Shuai, Zha Zhenggen, Wang Zhiyong. A Rapid and Efficient Access to Polysubstituted Imidazoles via Iodine-Catalyzed Tandem Oxidative Cyclization [J]. Acta Chimica Sinica, 2012, 70(23): 2408-2411.
[14]	Yang Yi, You Zhengwei, Qing Fengling. Design and Synthetic Investigation toward gem-difluoromethylenated Fostriecin Analogue [J]. Acta Chimica Sinica, 2012, 70(22): 2323-2336.
[15]	Xin Yang, Pi Zifeng, Song Fengrui, Liu Zhiqiang, Liu Shuying. Study on the Influence of Rhizoma Zingiberis on the Absorptive Profile of Aconite Alkaloids in the Rat Gut Sacs by Ultra Performance Liquid Chromatography-Mass Spectrometry [J]. Acta Chimica Sinica, 2012, 70(05): 551-560 .

若干D环带硝基的小檗因衍生物的光环化合成