Synthesis Of 2-benzoxanes And Isochromans With The Participation Of Electrophilic Organoselenium Reagents

2-Benzoxetine and isomerization as a basic structural unit with a variety of pharmaceutical and biological activities are widely found in various natural products.Studies have shown that compounds containing 2-benzoxepine structure usually have a certain anti-depressant activity,anti-bacterial bacterial activity,but also has a certain role in the treatment of neurodegenerative diseases;and multi-substituted heterochromatin The compounds exhibit high pharmacological activity in antihypertensive,analgesic and antihistamines.With the "anti-cancer king" reputation of organic selenium reagent,is a strong antioxidant,not only can enhance immunity,anti-aging,but also can remove the body of carcinogens free radicals,enhance the body's resistance to cancer and Improve the side effects of slowing down chemotherapy.Therefore,the use of organic selenium reagent biological activity characteristics and reaction characteristics,the synthesis of selenium functional 2-benzohee heptane and heterochromatic compounds,in order to find a both anti-inflammatory activity,but also has anti-cancer activity A variety of therapeutic effects of drugs.Under the protection of room temperature and nitrogen,under the catalysis of anhydrous boron trifluoride diethyl ether or anhydrous zinc chloride,with the weak nucleophilic N-phenyl selenophthalimide induced 3,4,5-trimethoxybenzyl cinnamyl ether undergoes intramolecular cyclization to form new carbon-carbon bonds and carbon-selenium bonds to synthesize the selenium functionalized 2-benzoxepine compounds,And then 30%of H2O2 for selenium oxidation elimination reaction,will be the corresponding olefin compounds.Since the reaction is achieved by the formation of organic selenium-induced carbon-carbon bonds at room temperature,the process has the advantages of easy operation,mild conditions,high selectivity and stereoselectivity,and higher yield.Method has a high research value.Under the protection of room temperature and nitrogen,boron trifluoride diethyl ether as catalyst,is still in the N-phenyl selenyl phthalimide induced by 3,4,5-trimethoxybenzyl cinnamyl ether Intramolecular cyclization reaction,the reaction time from 2 hours extended to 12 hours,the synthesis of a series of selenium functional group of heterochromatic compounds.The method has the advantages of easy operation,mild reaction conditions,high yield,regional selectivity and stereoselectivity.Through the study of the reaction mechanism,we found that with anhydrous zinc chloride as a catalyst,regardless of the length of time,only to stay in the formation of benzene seven ring.And boron trifluoride ether as a catalyst when the ring formed by the formation of benzoxycarbazepine ring will be further open ring to form a new selenium ion,and then rearrangement ring to form a more stable benzozaza six ring compounds.