Nikola M. Mollov

Synthesis of 5,7,11 b,12-tetrahydro-isoindolo[2,1-b]isoquinolinium methiodides and theirStevens rearrangement

The title compounds5 were synthetized in two steps from the corresponding isoindolo[2,1–b]isoquinoline-5(7H)-ones3, obtained in high yields from 3-ethoxy-1H-isoindoles2 and homopthalic anhydrides1. TheStevens rearrangement of5 gave 2-methyl-2,3-dihydro-1H-isoindole-1-spiro-2′-indanes6.ZusammenfassungDie Titelverbindungen5 wurden in zwei Stufen aus den entsprechenden Isoindolo[2,1–b]isochinolin-5(7H)-onen (3) dargestellt, die ihrerseits in hohen Ausbeuten aus 3-Ethoxy-1H-isoindolen (2) und Homophthalsäureanhydriden erhältlich sind. DieStevens-Umlagerung von5 führte zu 2-Methyl-2,3-dihydro-1H-isoindol-1-spiro-2′-indanen (6).

Synthesis and properties of glaucine-quinol

Abstract Glaucine-quinol(3) was prepared via electrophylic hydroxylation of glaucine(1) or predicentrine(2). Treatment of 3 with Ac2O and conc H2-SO4 resulted in 4 acetylshrilankine(4) and 2,4 diacetylshrilankine(5). Hydrolysis afforded shrilankine(6) and the following methylation cataline(8). 3 reacted with 48% HBr and conc H2SO4 to give 3-bromo-predicentrine(9). The diols 11 and 12 obtained on reduction of 3 were converted into dibenzoxazabicycloundecane(13). Dibenzoxepine(14) was the Hoffman degradation product of 14. On reduction with LAH 13 afforded dibenzoazacyclodecane(15). 3 on acetylation gave glaucine-quinol acetate(16) and acetoxydibenzoxazabicycloundecane (17).