Studies On The Photoinduced Cycloadditon Reactions Of 3-chloroisoquinolin-1-ones And 3-chloroquinolin-2-ones With Styrenes

As an important approach of carbon-carbon bond formation and carbon-heteroatom bond formation, photochemistry of organic halides has been studied extensively. This thesis mainly deals with the one-pot synthesis of benzo[a]phenanthridin-5-ones and benzo[k]phenanthridin-6-ones by photoinduced cycloaddition of 3-chloroisoquinolin-1-ones and 3-chloroquinolin-2-ones with styrenes. It consists of two parts:The first of this thesis is a concise introduction of three important mechanisms of organic halides in photochemistry. The highlight is the photoreactions of organic halides with carbanions, unsaturated hydrocarbon, aryl alkoxide and aryl amide anions, etc. Some of them aren't achieved by means of thermal reaction or catalytic reaction.The second part is the report of my research work. I examined the photoinduced cycloadditon 3-chloroisoquinolin-l-ones(la-c) and 3-chloro-l-methylquinolin-2-one(6a) with styrenes(2a-c),3-chloroisoquinolin-l-ones(la-c) with ethynylbenzene. And a novel and efficient procedure for the synthesis of benzo[a]phenanthridin-5-ones and benzo[k]î–£phenanthridin-6-ones has been achieved in moderate to high yields via photodechlorination-initiated coupling, photochemical elimination of HCl, photoisomerization, photocyclization and oxidation aromatization.