Synthesis of 1-Substituted Aminomethyl-7,8-didehydro-4-hydroxy-3,7- dimethoxy-17-methylmorphinan-6-one

Abstract

Under ultrasound irradiation, two new substituted aminomethyl derivatives of sinomenine 1a and 1b were synthesized at C-1 in A-ring through Mannich reaction. Furthermore, eight new substituted aminomethyl derivatives 2a～2h have been prepared by the amine exchange reaction of the compound 1a with aromatic amines or morpholine. The structures of the new compounds have been characterized by IR, MS, ¹H NMR and NOE spectra.

Key words: Mannich reaction, amine exchange reaction, sinomenine

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LUO Juan, ZENG Hong-Yao, LI Ying, YIN Shu-Fan*. Synthesis of 1-Substituted Aminomethyl-7,8-didehydro-4-hydroxy-3,7- dimethoxy-17-methylmorphinan-6-one[J]. Chin. J. Org. Chem., 2007, 27(05): 648-652.

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[1] Xuedan Wu, Ruixiang Xu, Xiaolong Fang, Kehua Zhang, Jie Jin. Design and Synthesis of N-Tetrazole and N-Oxadiazole Heterocyclic Derivatives of Sinomenine [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2506-2518.

[2] Yang Liu, Xiang Huang, Min Wang, Jian Liao. Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1499-1509.

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dinitrohexahydropyrimidine [J]. Chin. J. Org. Chem., 2010, 30(03): 409-413.

[14] WANG Min, LIANG Yan, SONG Zhi-Guo, JIANG Heng. Efficient One-Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Aluminium p-Toluenesulfonate under Mild Conditions [J]. Chin. J. Org. Chem., 2010, 30(02): 295-298.

[15] Song, Xiaoli ; Yan, Jufang; Fan, Li; Chen, Xin;
Xu, Jin ; Zhou, Zuwen; Yang, Dacheng*
. Synthesis and Preliminary Evaluation of Antidiabetic Activity of 4-(1-Aryl-3-aryl/arylalkyl-3-oxopropylamino)-N-(5-methyl- 3-isoxazolyl)benzene Sulfonamide [J]. Chin. J. Org. Chem., 2009, 29(04): 606-613.

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1-取代胺甲基-7,8-二去氢-4-羟基-3,7-二甲氧基-17-甲基-9α,13α,14α-吗啡烷-6-酮的合成

Synthesis of 1-Substituted Aminomethyl-7,8-didehydro-4-hydroxy-3,7- dimethoxy-17-methylmorphinan-6-one

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[1]	Xuedan Wu, Ruixiang Xu, Xiaolong Fang, Kehua Zhang, Jie Jin. Design and Synthesis of N-Tetrazole and N-Oxadiazole Heterocyclic Derivatives of Sinomenine [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2506-2518.
[2]	Yang Liu, Xiang Huang, Min Wang, Jian Liao. Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1499-1509.
[3]	Hui Li, Liang Yin. Research Progress of Copper-Catalyzed Direct Vinylogous Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1573-1585.
[4]	Zhang Shiju, Li Xiaotong, Wang Yan, Zheng Yucong, Han Shiqing, Yu Huilei, Huang Shahua. Formal Synthesis of Gram-Negative Antibiotic Negamycin [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 521-527.
[5]	Ye Jianliang, Huang Peiqiang. Progress in Heterocycles-Based Asymmetric Vinylogous Mannich Reactions and Applications to the Synthesis of Alkaloids [J]. Chin. J. Org. Chem., 2018, 38(9): 2215-2230.
[6]	Liu Yuting, Wu Qianqian, Yin Dawei, Li Diyang. Latest Progress and Application of Mannich Reaction [J]. Chin. J. Org. Chem., 2016, 36(5): 927-938.
[7]	Hui Yonghai, Shi Wei, Xie Shaolei, Wang Changchun, Xie Zhengfeng. Three-Component Mannich Reaction Catalyzed by MCM-41 Immobilized H₃PW₁₂O₄₀ (PW) in Water [J]. Chin. J. Org. Chem., 2014, 34(6): 1212-1217.
[8]	Liu Zhichang, Wang Yinghong, Zeng Hongyao, Nie Wanli, Xiang Qingxiang. Synthesis and Antibacterial Activities of Mannich Bases of Curcumin Derivatives [J]. Chin. J. Org. Chem., 2014, 34(11): 2345-2349.
[9]	LIU Wen-Jun, WANG Xin, LI Gang, YE Jia, CHENG Tie-Ming, LI Run-Tao. Synthesis and Analgesic Activity of Mono-spirocyclopiperazinium Analogues [J]. Chin. J. Org. Chem., 2011, 31(12): 2135-2139.
[10]	CHEN Jun-Li, JIE Zheng-Feng, XING Ye. Mannich Reaction of Acetophenone, Aromatic Aldehydes and Aro-matic Amines Catalyzed by Tungstophosphoric Acid in Water [J]. Chin. J. Org. Chem., 2011, 31(10): 1714-1718.
[11]	ZHANG Ping, HUANG Jin-Hua, WANG Lan-Zhi, LIU Wei, LI Yuan. Synthesis of Methyl 4-Substituted-phenyl-2,3-dihydro-1,5- benzothi-azepine-3-acetates and Their Sodium Salts [J]. Chin. J. Org. Chem., 2010, 30(12): 1939-1943.
[12]	ZHOU Jie-Wen, YAN Ju-Fang, TANG Xue-Mei, ZHANG Wei-Yu, ZHANG Yang-Xia, CHEN Xin, SU Xiao-Yan, YANG Da-Cheng. Synthesis and Preliminary Evaluation of Antidiabetic Activity for β-Amino Ketone Containing Isoxazole Moiety [J]. Chin. J. Org. Chem., 2010, 30(04): 582-589.
[13]	LI Qing-Xia, WANG Feng, MENG Wen-Jun, MENG Zi-Hui, LOU Zhong-Liang, SONG Gong-Yan, QIN Guang-Meng, GE Zhong-Hua, WANG Bo-Zhou. Reaction Mechanism for the Formation of 1,3-Ditertiobutyl-5,5- dinitrohexahydropyrimidine [J]. Chin. J. Org. Chem., 2010, 30(03): 409-413.
[14]	WANG Min, LIANG Yan, SONG Zhi-Guo, JIANG Heng. Efficient One-Pot Synthesis of β-Amino Ketone Derivatives Catalyzed by Aluminium p-Toluenesulfonate under Mild Conditions [J]. Chin. J. Org. Chem., 2010, 30(02): 295-298.
[15]	Song, Xiaoli ; Yan, Jufang; Fan, Li; Chen, Xin; Xu, Jin ; Zhou, Zuwen; Yang, Dacheng* . Synthesis and Preliminary Evaluation of Antidiabetic Activity of 4-(1-Aryl-3-aryl/arylalkyl-3-oxopropylamino)-N-(5-methyl- 3-isoxazolyl)benzene Sulfonamide [J]. Chin. J. Org. Chem., 2009, 29(04): 606-613.