123716-04-1Relevant articles and documents
Novel heterocycles from 5-methyldibenz[b,f]azocin-6,12-dione and its derivatives
Letcher, Roy M.,Kwok, Nai-Chiu,Lo, Wing-Hong,Ng, Kai-Wing
, p. 1715 - 1719 (2007/10/03)
The multifunctional dibenzazocine 2 and its benzylidene derivative 3 have been shown to take part in a variety of rearrangement reactions to produce novel heterocycles. Heterochrysenes 5 and 6 are formed from 3 on treatment with hydroxylamine and ethylamine respectively. The novel spiro-compounds 7 and 9 are obtained from 2 with aniline (at 120 °C) and NaIO4 (or SeO2) oxidation respectively, and acid and amine treatment of 2 gives the isocoumarin 10 and isoquinolines 8(a-c) respectively. Alkaline hydrolysis of 2 gives the deoxybenzoin 11 from which 5,7,8(a-c), 9 and 10 are also obtainable leading to mechanistic suggestions for the formation of these compounds. Treatment of 10 with Lawesson's reagent gives the thionoisocoumarin 13.