Synthesis of a Novel Triheterocyclic Framework via 1,3‐Dipolar Cycloaddition of a Nitrile Oxide with Imidazo[2,1‐b][1,3]thiazole‐3(2H)‐ones |
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| Authors: | Xiaofang Li Aiting Zheng Bin Liu Xianyong Yu Pinggui Yi |
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| Institution: | Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education and Hunan Province, College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and TechnologyXiangtan, , Hunan, 411201 China |
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| Abstract: | A novel series of (9Z)‐9‐arylmethylidene‐3‐(2,6‐dichlorophenyl)‐5,6‐dihydro1,3]thiazolo2′,3′:2,3]imidazo 1,2‐d]1,2,4]oxadiazol‐8(9H)‐one derivatives were prepared in moderate yields by the 1,3‐dipolar cycloaddition reaction of a nitrile oxide with (2Z)‐2‐arylmethylidene‐5,6‐dihydroimidazo 2,1‐b]1,3]thiazol‐3(2H)‐ones. The reaction site of the dipolarphile is the C═N of imidazo2,1‐b]1,3]thiazole rather than the expected C═C of the arylmethylidene. The product structures were characterized thoroughly by IR, MS, NMR spectroscopy, and elemental analysis. The results indicate that this reaction proceeds with chemoselectivity and regioselectivity. |
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