The Synthesis of 3-Arylaminomethyl-2,4-dihydroxyacetophenone or 8-Acetyl-3-aryl-3,4-dihydro-5-hydroy-2H-1,3-benzoxazine and Their Interconversion

Chem. J. Chinese Universities ›› 1995, Vol. 16 ›› Issue (5): 730.

• Articles • Previous Articles Next Articles

The Synthesis of 3-Arylaminomethyl-2,4-dihydroxyacetophenone or 8-Acetyl-3-aryl-3,4-dihydro-5-hydroy-2H-1,3-benzoxazine and Their Interconversion

ZHU Zhi-Hong, XU Xiu-Juan

Department of Chemistry, Beijing Normal University, Beijing, 100875

Received:1994-05-26 Revised:1995-01-15 Online:1995-05-24 Published:1995-05-24

Abstract

Abstract: The Mannich reaction of 2,4-dihydroxyacetophenone, 37% formaldehyde solution and arylamines has been studied in ethanolic-HCl solution or 95% ethyl alcohol. Two differ ent kinds of compounds are obtained. Five 3-arylamino-methyl-2,4-dihydroxy (5) and five sacetyl-3-aryl-3,4-di-hydro-5-hydroxy-2H-1, 3-benzoxazine (6) are prepared.All of them are first reported. The structures of sand 6 are deduced by elemental analysis,IR,¹H NMR,MS and UV analysis. The interconversion between₅and 6 has also been real ized successfully.

Key words: Mannich reaction, Mannich base, 3-Arylaminomethyl-2,4-dihydroxyace tophenone, 8-Acetyl-3-aryl-3,4-dihydro-5-hydroxy-2H-1,3-benzoxazine, 2,4-Dihydroxyacetophenone

CLC Number:

O625

TrendMD:

ZHU Zhi-Hong, XU Xiu-Juan . The Synthesis of 3-Arylaminomethyl-2,4-dihydroxyacetophenone or 8-Acetyl-3-aryl-3,4-dihydro-5-hydroy-2H-1,3-benzoxazine and Their Interconversion[J]. Chem. J. Chinese Universities, 1995, 16(5): 730.

[1]	ZHANG Yan, WANG Baolei, ZHAN Yizhou, ZHANG Liyuan, LI Yonghong, LI Zhengming. Synthesis and Biological Activities of Novel 5-(Pyridine-3-yl)-1,2,4-triazole Mannich Bases and Bis-Mannich Bases Containing Piperazine Moiety^† [J]. Chem. J. Chinese Universities, 2016, 37(6): 1100.
[2]	XIONG Zhen, JI Siping, CHUAN Yongming, JIANG Lin, YUAN Minglong. Synthesis Method of β-Aminophosphonate Derivatives^† [J]. Chem. J. Chinese Universities, 2015, 36(6): 1112.
[3]	BU Huijuan, ZHANG Jing, MU Boshuai, LI Yuan. Mannich Reaction of Aromatic Ketones Based on Acetic Acid as Solvent and Catalyst^† [J]. Chem. J. Chinese Universities, 2014, 35(9): 1912.
[4]	SHEN Shengqiang, SUN Xiaohong, LIU Yuanfa, CHEN Bang, JIN Ruyi, MA Haixia. Synthesis and Biological Activity of 1,3,4-Oxadiazole Mannich Bases Containing Pyrimidine Rings^† [J]. Chem. J. Chinese Universities, 2014, 35(7): 1427.
[5]	MA Xue-Lin, ZHANG Xiao-Yong, YONG Sheng-Li, DUAN Li-Ping, WU Zhen-Yu. Synthesis of Multiaryl-substituted Mannich Base Catalysed by Silica-supported Rare Earth Samarium Chloride [J]. Chem. J. Chinese Universities, 2013, 34(12): 2759.
[6]	SONG Zhi-Cheng, WANG Shi-Sheng, SONG Qi-Ling, SHU Tao, ZHAO Wei-Jie. Synthesis and α-Glucosidase Inhibitory Activity of Oleanolic Acid Derivatives [J]. Chem. J. Chinese Universities, 2012, 33(04): 744.
[7]	YANG Da-Cheng, ZHANG Guo-Lin, YANG Yu, ZHONG Yu-Guo . The Mannich Reaction of 4-Methylacetophenone with Aromatic Aldehydes and Aromatic Amines [J]. Chem. J. Chinese Universities, 2000, 21(11): 1694.
[8]	WANG Bing-Xiang, HU Jia-Xin, HU Yue-Fei, HU Hong-Wen . A Facile Onestep Synthesis of 1-Acylindolizines by the Reaction of Pyridinium Salts with Mannich Bases in the Presence of TPCD [J]. Chem. J. Chinese Universities, 1999, 20(3): 418.
[9]	WANG Zhong-Yi, YOU Tian-Pa, SHI Hai-Jian, SHI Hao-Xin. Studies on Double Mannich Reaction of 3-Aryl-5-mercapto-1, 2, 4-triazoles [J]. Chem. J. Chinese Universities, 1997, 18(4): 550.
[10]	QI Chuan-Min, JI Zhi-Zhong, LI Yu-Lan, WANG Biao. Synthesis and Antiinflammatory Activity of 2-Alkyl Cyclopentenone Derivatives [J]. Chem. J. Chinese Universities, 1996, 17(2): 258.
[11]	WANG Jin, ZHOU Xun-Jun, DU Shao-bin . Reactions Between Sodium Hydrogen Telluride and Aminoalkylbenzotriazoles [J]. Chem. J. Chinese Universities, 1992, 13(4): 493.
[12]	Chen Ru-yu, Feng Ke-sheng . Syntheses of 2,5-Diphenyl-3,3-disubstituted-2,3-dihydro-1,4,2-oxazaphosphole-2-oxides by Mannich Reaction [J]. Chem. J. Chinese Universities, 1991, 12(12): 1605.

The Synthesis of 3-Arylaminomethyl-2,4-dihydroxyacetophenone or 8-Acetyl-3-aryl-3,4-dihydro-5-hydroy-2H-1,3-benzoxazine and Their Interconversion

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 12

Recommended Articles

Metrics

Comments