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

通过2-芳亚甲基-6,7-二氢-5H-噻唑并[3,2-a]嘧啶-3-酮(1a～1j)与甲亚胺叶立德(经靛红与肌氨酸反应原位生成)进行的l,3-偶极环加成反应,合成了10个新的螺噻唑并[3,2-a]嘧啶类化合物2a～2j.采用NMR、质谱、IR、元素分析以及X射线单晶衍射等多种谱学技术对产物2a～2j进行了结构表征,研究结果表明此类反应具有高度的立体选择性和区域选择性.

A new class of spiro thiazolo[3,2-α]pyrimidine compounds 2a-2j were synthesized by the 1,3-dipolar cycloaddition reaction of 2-arylmethylidene-6,7-dihydro-SH-thiazolo[3,2-α]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.