基于甲亚胺叶立德的[3+2]和[3+3]环加成反应
毕业论文关键词：甲亚胺叶立德、环加成反应、串联反应、杂环骨架
Abstract Nitrogen-containing heterocyclic compounds exist widely in natural products and drug molecules. These compounds tend to have unique biological and pharmacological activities. Therefore, the synthesis of of this type of compounds is an important source of lead molecules for drug development. In this dissertation, two kinds of heterocyclic skeletons with unique biological activity were constructed based on the cycloaddition reactions of azomethine ylide. In the first chapter, we introduce the research background of the organocatalytic asymmetric 1,3-dipolar cycloadditions (1,3-DC) of azomethine ylide. Besides, the research objectives and contents of this dissertation were also introduced. In the second chapter, we introduced the enantioselective construction of spiro[indoline-3,2’-pyrrole] framework via catalytic asymmetric 1,3-dipolar cycloadditions using allenes as equivalents of alkynes. In this allene-involved 1,3-DC, an unexpected spirooxindole framework bearing an intra-annular C=C double bond was generated, which is quite different from previously reported 1,3-DCs of allenes. This approach not only confronted the great challenge in using allenes as dipolarophiles of 1,3-DCs, but also provided a unique strategy of using allenes as equivalents of alkynes to construct spiro[indoline-3,2’-pyrrole] structure. Besides, this reaction also represents the first catalytic asymmetric ketone-involved 1,3-DCs of allenes, which will also greatly enrich the research contents of 1,3-DCs, the chemistry of allenes as well as the synthetic methods of spirooxindoles. In the third chapter, we introduced a chemoselective [3+3] cycloaddition of in situ generated azomethine ylides with quinone monoimides (QMIs), which efficiently constructed six-membered dihydrobenzoxazine frameworks with biological relevance in excellent chemoselectivities and high yields (up to >95:5 cr, 98% yield). This reaction not only represents the first [3+3] cycloaddition of QMIs, but also provides a new example for [3+3] cycloadditions of azomethine ylides by using oxygen-contained dipolarophiles, which will serve as a useful strategy in constructing dihydrobenzoxazine scaffold.
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