75519-74-3Relevant academic research and scientific papers
Reactions of Spiro-indazoles containing Keto-groups. Syntheses of Benzaceanthrylenes, Naphthaceanthrylenes, and Fluoranthenes
Hirakawa, Kioyoichi,Toki, Takuya,Yamazaki, Kazuo,Nakazawa, Sho
, p. 1944 - 1949 (2007/10/02)
Anthrone-10-spiro-3'-3'H-imidazole (1) and 3H-indazole-3-spiro-1'-naphthalen-4'(1'H)-one (3), prepared by the cycloaddition of benzyne with 10-diazoanthrone (6) and 4-diazanaphthalen-1(4H)-one (7), respectively, thermally rearranged with elimination of nitrogen to 8-hydroxybenzaceanthrylene (9b) and 3-hydroxyfluoranthene (11b), respectively.The diazoketone (6) reacted with 1,2-naphthyne to give anthrone-10-spiro-3'-3'H-benzindazole (4) and anthrone-10-spiro-1'-1'H-benzindazole (5), which gave the rearrangement product, 10-hydroxynaphthaceanthrylene (12b) by thermolysis.Photolysis of the spiro-indazoles afforded the rearrangement and/or photo-oxidation products.Thermolysis and photolysis are accountable on the basis of formation of biradicals and isomerization of these to fused polycyclic compounds.In particular, the isomerization of the biradical (21) to (12b) involves the formation of the naphthocyclopropene (20).
