含有吲哚结构单元的四环化合物的高选择性合成研究-有机化学专业论文.docxVIP

AB AB STRACT In this thesis，several highly efficient and novel methodologies for the preparation of indole-containing tetracyclic compounds (such indolo[1，2-c】quinazolines， 1 IH-indolo[3，2．c]quinolines， 6H-isoindolo[2，1一a]indol-6一ones and indeno[1，2一b]indol-10(5／-／)-ones)have been successfully developed through copper／l：Ialladium-catalyzed cascade reactions of 2-(2一bromoaryl)-IH-indoles with different reaction partners．The main research results are follows： Firstly,highly regioselective synthesis of indolo[1，2一c]quinazolines and 1 1H-indolo[3，2-c]quinolines through copper-catalyzed one-pot two—step three-component cascade reaction of 2-(2-bromoaryl)一1H-indoles with aldehydes and aqueous ammonia has been successfully realized by simply tuning the pH value of the reaction system．The reaction results indicated that under nitrogen atmosphere，the copper-catalyzed cascade reaction of 2-(2一bromoaryl)一1H-indoles with aldehydes and aqueous ammonia firstly afford 5,6一dihydmindolo[1，2一c]quinazolines key intermediates，and then heating the reaction mixture under air could give rise to indolo[1，2-c]quinazolines in highly regioselective manner；whereas adjusting the pH value of the reaction system to range of 5-6 followed by heating the resulting mixture under air could regioselectively afford 1 1H-indolo[3,2-c]quinolines． Secondly,we have also developed highly selective and new method for the preparation of 6H-isoindolo[2，1-a]indol-6一ones and indeno[1，2-b]indol一10(5／-／)一ones via palladium-catalyzed cyclocarbonylation reaction of 2-(2一bmmoaryl)一indoles with CO C 1 source．Notably,the regioselectivity Can be easily controlled by employing different substrates．With 2-(2-bromoaryl)-1H-indoles reactants， this reaction could regioselectively afford 6H-isoindolo[2，1-a]indol-6一ones， whereas indeno[1，2一b]indol·10(5H)一ones could be obtained in highly selective manner by using N-substituted 2-(2-bromoaryl)-1H-indoles as substrates． KEYWORDS：Indole—containing tetracyclic compound,Copper／palla