Synthesis of 8-Aryl-substituted 4-amino-6-chloro-8H-pteridin-7-one

Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (10): 1830-1835. Previous Articles Next Articles

Reports

N8-芳基取代4-氨基-6-氯-7(8H)-蝶啶酮的合成

段崇刚^a,b ; 徐为人^c ; 汤立达^c ; 贾炯^a ; 王建武^*,a

(a山东大学化学与化工学院济南 250100)
(b山东省医药工业研究所济南 250100)
(c天津药物研究院天津 300193)

收稿日期:2008-01-02 修回日期:2008-05-08 发布日期:2008-10-20
通讯作者: 王建武

Synthesis of 8-Aryl-substituted 4-amino-6-chloro-8H-pteridin-7-one

DUAN, Chong-Gang ^a,b ; XU, Wei-Ren ^c; TANG, Li-Da ^c ; JIA, Jiong ^a ; WANG, Jian-Wu^*,a

(a College of Chemistry and Chemical Engineering, Shandong University, Jinan 250100) (b Shandong Institute of Pharmaceutical Industry, Jinan 250100)
(c Tianjin Institute of Pharmaceutical Research, Tianjin 300193)

Received:2008-01-02 Revised:2008-05-08 Published:2008-10-20
Contact: WANG, Jian-Wu

Abstract

A series of novel 8-aryl substituted 4-amino-6-chloro-8H-pteridin-7-one derivatives were synthesized by cyclization of 4-[(un)substituted anilino]-5,6-diaminopyrimidine with oxalic acid dihydrate and subsequent chlorination. Their structures were confirmed by 1H NMR, 13C NMR, IR, ESI-MS and elemental analysis. The structure of 4-amino-6-chloro-8-p-tolyl-8H-pteridin-7-one (3a) was further determined by X-ray crystallographic analysis, providing a proof of the regioselectivity in the related cyclization reaction.

Key words: oxalic acid, triaminopyrimidine, cyclization, synthesis, pteridinone

Cite this article

DUAN, Chong-Gang ^a,b ; XU, Wei-Ren ^c; TANG, Li-Da ^c ; JIA, Jiong ^a ; WANG, Jian-Wu^*,a
. Synthesis of 8-Aryl-substituted 4-amino-6-chloro-8H-pteridin-7-one[J]. Chin. J. Org. Chem., 2008, 28(10): 1830-1835.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.
[2]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[3]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[4]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[5]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[6]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[7]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[8]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[9]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[10]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[11]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[12]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[13]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[14]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[15]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.

N8-芳基取代4-氨基-6-氯-7(8H)-蝶啶酮的合成

Synthesis of 8-Aryl-substituted 4-amino-6-chloro-8H-pteridin-7-one

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments