Study On The Synthesis Of Nitrogen Containing Heterocycles By Tandem[3+2]Cycloaddition Reaction

In this paper,a series of indo[1’,2’:2,3]chromeno[3,4-c]pyrrole derivatives,indo-2’-cyclopentane[b]benzofuran-2’,3’-Indoline derivatives,spiro[cyclopropyl[c]benzo-1,2’-indene]derivatives,benzofuran[2’,3’:1,5]cyclopentane derivatives spiro[indole-3,4’-pyridine]derivatives,spiro[cyclopentane-1,3’-Indoline]derivatives and cyclopentane[c]quinoline derivatives.First,the cycloaddition reaction of three components of amino acid or glycine ester,Acetylenedicarboxylic acid diester and 2-o-hydroxyphenylmethylene indandione at room temperature,ethanol as solvent,Et3N as base,was studied.The products were 1-indo[1’,2’:2,3]chromeno[3,4-c]pyrrol-3-carboxylic acid ethyl derivatives,14 indo[1’,2’:2,3]chromeno[4,3-a]pyrrolizine derivatives and spiro[dihydroindole-3,4’-pyran]derivatives.Different substituents of o-hydroxyphenylmethylene exhibit similar reactivity.A total of 35 new compounds that have not been reported have been synthesized.Secondly,under different reaction conditions(alkali and solvent),the two component reactions of indigo MBH ester with 2-o-hydroxybenzenemethylindenedione were studied.Different structures of indigo MBH esters exhibited different reactivity and product structures.The products include cis/trans isomerized dihydro[indene-2’-cyclopentane[b]benzofuran-2’,3"-indoline]-3’-nitrile,cis-dihydroindene-2’-cyclopentane[b]benzofuran-2’,3"-indoline]-3’-carboxylic acid derivatives,spiro[cyclopropyl[c]benzo-1,2’-indene]-2-carboxylic acid ethyl derivatives,dihydroindene-2,5’-benzofuran[2’,3’:1,5]cyclopentane[1,2-c]pyrrol-4’,3’-Indoline derivatives were synthesized and 64 new compounds were synthesized.Finally,the[3+3]cycloaddition reaction of aromatic amine,acetylenedicarboxylic acid diester and indigo MBH ester with DABCO as base and dichloromethane as solvent was studied at room temperature,and the products were spiro[indole-3,4’-pyridine]derivatives.At the same time,the two-component reaction of indigo MBH ester with acetylenedicarboxylic acid diester was studied.The products were different under different reaction conditions,including spiro[cyclopentane-1,3’-Indoline]-2,4-diene derivatives and cyclopentane[c]quinoline derivatives.A total of 31 new compounds that have not been reported have been synthesized.The structures of the synthesized compounds were characterized by IR,HRMS,1H NMR,13C NMR,and the single crystal structures of 18 of them were determined.