123716-04-1Relevant academic research and scientific papers
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.
Reactions of an Indenoindole and Novel Rearrangements of a Dioxodibenzazocine to Derivatives of 5,12-Diaza- and 5-Oxa-12-aza-chrysene
Letcher, Roy M.,Ng, Kai-Wing,Cheung, Kung-Kai
, p. 1602 - 1603 (2007/10/02)
Oxidation of 10-benzylidene-5-methyl-5,10-dihydroindenoindole (2) gives the dioxodibenzazocine (3), which reacts (probably via a transannular interaction) with hydroxylamine and with ethylamine to give oxa-aza- and diaza-chrysene derivatives (5) and (6); the X-ray crystal structure of (5) is reported.
