Synthesis of Spiro Thiazolo[3,2-a]pyrimidine Compounds by 1,3-Dipolar Cycloaddition Reaction

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (05): 735-739. Previous Articles Next Articles

Notes

1,3-偶极环加成反应合成螺噻唑并[3,2-a]嘧啶类化合物

李筱芳*^{,1,2，于贤勇¹，冯亚青²}

(¹湖南科技大学化学化工学院湖南科技大学理论化学与分子模拟省部共建教育部重点实验室
分子构效关系湖南省普通高等学校重点实验室湘潭 411201)
(²天津大学化工学院应用化学系天津 300072)

收稿日期:2009-08-19 修回日期:2009-10-30 发布日期:2009-12-14
通讯作者: 冯亚青 E-mail:yqfeng@tju.edu.cn
基金资助:
国家级.国家自然科学基金

Synthesis of Spiro Thiazolo[3,2-a]pyrimidine Compounds by 1,3-Dipolar Cycloaddition Reaction

Li Xiaofang*^{,1, 2 Yu Xianyong¹ Feng Yaqing²}

(¹ Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201)
(² School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072)

Received:2009-08-19 Revised:2009-10-30 Published:2009-12-14
Contact: Feng Yaqing E-mail:yqfeng@tju.edu.cn

Abstract

A new class of spiro thiazolo[3,2-a]pyrimidine compounds 2a～2j were synthesized by the 1,3-dipolar cycloaddition reaction of 2-arylmethylidene-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-one (1a～1j) with azomethine ylide (generated in situ by the reaction of isatin with sarcosine). The structures of the products 2a～2j were determined and characterized thoroughly by NMR, MS, IR techniques, elemental analysis, and X-ray crystallographic analysis. The results of experiment indicated that this 1,3-dipolar cycloaddition proceeded with high stereoselectivity and regioselectivity.

Key words: thiazolo[3,2-a]pyrimidine, azomethine ylide, 1,3-dipolar cycloaddition, stereoselectivity and regioselectivity

Cite this article

LI Xiao-Fang, YU Xian-Yong, FENG Ya-Qing. Synthesis of Spiro Thiazolo[3,2-a]pyrimidine Compounds by 1,3-Dipolar Cycloaddition Reaction[J]. Chin. J. Org. Chem., 2010, 30(05): 735-739.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.
[2]	Huachao Liu, Chong Shen, Xin Chang, Chunjiang Wang. Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloaddition Reactions with Kinetic Resolution [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3322-3334.
[3]	Yue Guizhou, Liu Bo. Research Progress on [3+n] (n≥3) Cycloaddition of 1,3-Diploes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3132-3153.
[4]	Wei Liang, Xiao Lu, Hu Yuanzheng, Wang Zuofei, Tao Haiyan, Wang Chunjiang. Recent Advances in Metallated Azomethine Ylides for the Synthesis of Chiral Unnatural α-Amino Acids [J]. Chin. J. Org. Chem., 2019, 39(8): 2119-2130.
[5]	Meng Zhiying, Gu Mengmeng, Wang Mengyao, Xu Jing, Gao Xu, Hao Ganlu, Rong Liangce. An Efficient Synthesis of New Azomethine Ylide: 1-(Diaminomethyl-eneammonio)(aryl) methyl-4,4-dimethyl-2,6-dioxocyclohexan-1-ide under Solvent-Free Conditions [J]. Chin. J. Org. Chem., 2017, 37(1): 213-217.
[6]	Li Xiaofang, Yi Rongqiong, Liu Bin, Li Zhikui, Yu Xianyong, Yi Pinggui. Synthesis of Novel Spiro Indolizidine Derivatives via 1,3-Dipolar Cycloaddition of Azomethine Ylide [J]. Chin. J. Org. Chem., 2012, 32(12): 2309-2314.
[7]	Li, Xiaofang ^a,b; Yu, Xianyong ^a ; Feng, Yaqing^*,b. Regio- and Stereo-selective Synthesis of Novel Spirooxindole Compounds [J]. Chin. J. Org. Chem., 2009, 29(07): 1129-1132.
[8]	ZHENG Da-Gui*^,a, XIAO Zhu-Ping^a, LI Yu-Liang^b. A New Reaction for the Generation of Carbene from α-Amino Acid and Ketone [J]. Chin. J. Org. Chem., 2007, 27(12): 1609-1611.
[9]	WANG Feng, BAI Dong-Lu*. Recent Progress in [3＋2] Cycloaddition Using Azomethine Ylide [J]. Chin. J. Org. Chem., 2006, 26(01): 9-18.

1,3-偶极环加成反应合成螺噻唑并[3,2-a]嘧啶类化合物

Synthesis of Spiro Thiazolo[3,2-a]pyrimidine Compounds by 1,3-Dipolar Cycloaddition Reaction

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 9

Recommended Articles

Metrics

Comments