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Chinese Journal of Organic Chemistry 2010, 30(05) 735-739 DOI:
ISSN: 0253-2786 CN: 31-1321/O6 |
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Synthesis of Spiro Thiazolo[3,2-a]pyrimidine Compounds by 1,3-Dipolar Cycloaddition Reaction |
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Li Xiaofang*,1, 2 Yu Xianyong1 Feng Yaqing2 |
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(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) |
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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. |
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Keywords：
thiazolo[3,2-a]pyrimidine
azomethine ylide
1,3-dipolar cycloaddition
stereoselectivity and regioselectivity
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Received 2009-08-19 Revised 2009-10-30 Online: 2009-12-14 |
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Corresponding Authors: Feng Yaqing |
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Email: yqfeng@tju.edu.cn |
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