本论文包含两部分研究工作。第一部分工作研究了氮杂环卡宾（NHCs）催化下邻位缺电子烯基取代芳香醛与亚硝基芳烃之间的串联aza-Benzoin和分子内oxo-Michael加成反应。研究发现，在三唑卡宾催化作用下，邻位乙烯基芳香醛与亚硝基化合物首先发生分子间aza-Benzoin反应，接着进行分子内oxo-Michael加成反应，得到2，3-苯并噁嗪－4－酮衍生物，产率为63-92%。此部分工作总共合成了19个新化合物，所有产物都进行了IR、1H NMR、13C NMR、元素分析和MS或者HRMS鉴定。其中一个产物进行了单晶衍射分析。另外，我们还对几个2，3-苯并噁嗪－4－酮－1－乙酸酯产物进行了还原衍生化探索，在两种不同的还原条件下，苯并噁嗪－4－酮－1－乙酸酯可以被还原成新型的β-羟基羧酸酯衍生物或者3-氧代-1-异苯并呋喃乙酸酯衍生物。本研究不仅提供了一种简单有效的方法合成2，3-苯并噁嗪－4－酮类化合物，而且拓展了NHCs在催化形成碳-杂键和杂-杂键中的应用。第二部分工作研究了NHCs催化肉桂醛、亚硝基化合物和乙烯基酮之间的三组分串联分子间aza-Benzoin和oxo-Michael反应。研究发现，在三唑卡宾催化下，肉桂醛、亚硝基芳烃和乙烯基酮发生串联的三组分分子间aza-Benzoin和oxo-Michael加成反应，生成N－芳基－N－羰乙氧基肉桂酰胺（主产物），以及肉桂醛与亚硝基芳烃之间aza-Benzoin反应生成的N－芳基－N－羟基肉桂酰胺（副产物）。本部分工作共得到11个主产物和8个副产物，除了部分已知结构的副产物外，其它产物都进行了IR、1H NMR、13C NMR、EA和MS或者HRMS鉴定，并对一个主产物进行了单晶衍射分析。此研究不仅提供了一种简单有效的方法一锅合成N，N－二取代的肉桂酰胺衍生物，而且还拓展了氮杂环卡宾催化在多组分反应领域中的应用。

This thesis contains two parts of work.In the first part, the tandem intermolecular aza-benzoin and intramolecular oxo-Michael reaction of o-vinylarylaldehydes and nitrosoarenes catalyzed by NHCs were studied. It showed that electron-deficient o-vinylarylaldehydes underwent tandem intermolecular aza-benzoin and intramolecular oxo-Michael addition reaction with nitrosoarenes catalyzed by NHCs afforded correspounding 2,3-benzoxazin-4-one derivatives with 63-92% yield. This work furnished 19 novel compounds. All new compounds were characterized by NMR, IR, MS, and elemental analysis (or HRMS), and the structure of one product was also demonstrated by single-crystal X-ray diffraction analysis. The resulting 1-acetate substituted 2,3-benzoxazinones were transformed into a new type of β-hydroxycarboxylate derivatives or 3-oxo-1-isobenzofuranacetates, respectively, under different reductive conditions. This work not only provides a simple and efficient method for the construction of multifunctional 2,3-benzoxazin-4-ones of potential pharmacological interest, but also expands the application of NHC-catalyzed cascade reactions in the formation of carbon–heteroatom and heteroatom–heteroatom bonds.In the second part, a multicomponents cascade intermolecular aza-benzoin and oxo-Michael reaction of cinnaldehyde, nitrosoarenes and aryl(vinyl)ketone catalyzed by NHCs were studied. It revealed that a cascade intermolecular aza-benzoin and oxo-Michael addition reaction of cinnaldehyde, nitrosoarenes and aryl(vinyl)ketone catalyzed by NHCs gave the 1+1+1 major products N-(3-Oxo-3-aryl-propyl) -N-aryl-acrylamide and minor products of N-hydroxy-N-aryl-acrylamide. Totally, 11 major products and 8 minor products were obtained. All of them were fully characterized by NMR, IR, HRMS,except several known ones. Moreover, one of the major products was demonstrated by single-crystal X-ray diffraction analysis.This work not only provides a efficient method for the construction of N,N-disubstituded cinnamide in one pot with some simple materials, but also extends the application of NHC-catalyzed cascade multicomponents reactions.