1,3-偶极环加成反应已经在合成五元杂环中显示了极佳的应用前景，但是利用偶极子腈亚胺参与的1,3-偶极环加成反应来合成区域选择性的吡唑类衍生物仍极具挑战。在本课题中,我们将采取多样性导向的有机合成策略，通过原位生成的腈亚胺参与的环加成反应来构建吡唑类衍生物:(1)设计合成一些具有张力的环丙烯及环辛炔衍生物作为亲偶极体，通过环张力来促进普通烯烃及炔烃与腈亚胺的环加成反应；(2)发展其它一些高活性的亲偶极体，如芳炔、烯酮等与腈亚胺的新型1,3-偶极环加成反应；(3)采用底物结构修饰与金属催化策略，探索普通炔烃及环丙烷衍生物与腈亚胺的1,3-偶极环加成反应。项目预期将提供一条多样性导向合成吡唑类杂环的新路径，为含吡唑类药物中间体的合成提供具有实际应用价值的方案，丰富有机合成反应方法学。

1,3-Dipolar cycloaddition reactions play a pivotal role in the area of heterocycles synthesis. However, regioselective synthesis of the pyrazole ring via the 1,3-dipolar cycloaddition reaction of nitrile imine with multiple-bond remains a significant challenge for organic chemists. In this proposal, we will focus on diversity-oriented constructions of pyrazole scaffolds through the 1,3-dipolar cycloaddition between nitrile imine dipolars with dipolarophiles: (1) design and synthesize some strained cyclopropenes and cyclooctynes, then explore the cycloaddition reactions induced by the ring-strain; (2) examine the reactivity of a range of 1,3-dipolarophiles toward nitrile imine, such as arynes and ketenes; (3) evaluate the reactivity of alkynes or cyclopropane derivatives with nitrile imines promoted by modified substrates and metal. Ultimately, we hope to provide a facile and practical protocol for synthesis of diverse pyrazole, as well as drug intermediates.