154550-15-9Relevant academic research and scientific papers
PHOTOINDUCED MOLECULAR TRANSFORMATIONS. PART 147. PHOTOADDITION OF PROTECTED 4-HYDROXY-1(2H)-ISOQUINOLINONE WITH AN ELECTRON-DEFICIENT ALKENE AND THE FORMATION OF A 3,6-EPOXY-3,4,5,6-TETRAHYDRO-2-BENZAZOCIN-1(2H)-ONE VIA A β-SCISSION OF CYCLOBUTANOXYL RADICALS GENERATED FROM TH...
Suginome, Hiroshi,Kajizuka, Yoshinori,Suzuki, Masayoshi,Senboku, Hisanori,Kobayashi, Kazuhiro
, p. 283 - 288 (2007/10/02)
The direct irradiation of 4-benzyloxycarbonyloxy-2-methyl-1(2H)-isoquinolinone gave a 1 to 1 ratio of two stereoisomers of photoadducts in 97percent yield.Removal of the protecting group from the adducts by hydrogenolysis gave the corresponding cyclobutanols, (1α,2aα,8bα)-(+/-)-1-cyano-1,2a,3,8b-tetrahydro-8b-hydroxy-3-methylcyclobutisoquinolin-4(2H)-one and its (1α,2aβ,8bβ)- isomer in 78 and 67percent yields.The photolysis of the hypoiodite generated in situ from the (1α,2aα,8bα)-(+/-)-cyclobutanol with mercury(II) oxide - iodine in benzene induced a regioselective β-scission at the ring fusion bond of the cyclobutanoxyl radical to give 5-cyano-3,6-epoxy-3,4,5,6-tetrahydro-6-hydroxy-2-methyl-2-benzazocin-1(2H)-one in 76percent yield.The cyano substituent and the amide nitrogen play a decisive role in directing the bond to be cleaved.
