Isocyanide Involved Multicomponent Domino Synthesis Of Fused Pyrroles And Furans

Multicomponent domino reactions have been an important means to build compounds with complex unique structure,it is also one of the forefront and hot topic of chemical research nowadays.Three series of isocyanide-involving multicomponent domino reactions are studied systematically in this dissertation,and several new methods for the synthesis of heterocyclic compounds are developed.This thesis is divided into four parts:The first part introduces the advances in multicomponent domino reactions.The research progress of the multicomponent domino reactions based on isocyanides.In addition,the basis and significance of this paper,the main innovation points and the research methods of this paper are introduced.The second section involves an unprecedented cobalt(II)/silver co-catalyzed bicycloaddition of arylethynylanilines with isonitriles,by which a wide range of functionalized pyrrolo[2,3-b]indoles can be expediently and stereoselectively synthesized in a convergent manner.The reaction also features Co/Ag bimetallic catalysis,flexible structural modification,reliable scalability and mild reaction conditions.This method provides a new strategy to the rapidly construct the complexity and diversity structure of pyrrolo[2,3-b]indoles.The third section reports a novel isocyanide-based three-component bicyclization for the stereoselective synthesis of densely functionalized pyrano[3,4-c]pyrroles.The reaction offers a facile and practical pathway to access a wide range of densely functionalized pyrano[3,4-c]pyrroles in a highly diastereoselective and convergent manner.The present transformation involved Huisgen 1,3-dipole formation,Passerini-type reaction,and Mumm rearrangement as well as an oxo-Diels–Alder reaction sequence,resulting in the formation of two new rings and six new chemicalbonds including C–N,C–O and C–H bonds.This protocol also features flexible structural modification,excellent atom economy,high synthetic efficiency,and mild reaction conditions.This protocol provides a useful tool to the rapidly construct the complexity and diversity structure of pyrano[3,4-c]pyrroles.The forth part presents a new diazo compound-based three-component bicyclization for the efficient synthesis of various indeno[1,2-c]furans.The reaction is easy to perform simply by mixing three common reactants like phthalaldehydes,?-diazo arylketones and isocyanides,in the presence of weak base.This method is simple,avoiding the use of metal catalyst,which provides a new synthetic strategy to construct a wide range indeno[1,2-c]furans through bicyclization.All the structures of the resulting products were fully determined by their IR,NMR,HRMS.Possible mechanisms were also proposed.The above these studies provide new and effective methods for the synthesis of potentially bioactive aza-and oxa-heterocyclic compounds.