Unexpected nitrilimine cycloaddition of thiazolo[3,2-a]pyrimidine derivatives |
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| Authors: | Bin Liu Xiao-Fang LiXian-Yong Yu |
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| Affiliation: | 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, Hunan 411201, China |
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| Abstract: | 1,3-Dipolar cycloaddition of 2-arylidene-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-3(5H)-ones to diphenylnitrilimine (generated in situ by triethylamine dehydrohalogenation of the N′-phenylbenzohydrazonoyl chloride) proceeded regio- and site-selectively affording a mixture of two unexpected isomer products at reflux temperature. The cycloaddition/ring-opening/rearrangement/substitution, mechanism of the reaction was also discussed. |
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| Keywords: | 1,3-Dipolar cycloaddition Diphenylnitrilimine Thiazolo[3,2-a]pyrimidine Pyrrolo[1,2-a][1,2,4]triazolo[3,4-b]pyrimidine Thiazolo[3,2-a][1,2,4]triazolo[3,4-b]pyrimidine |
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