ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Heterocyclopolyaromatics, XII. Condensation of 3-(1-Imidazolyl)- and 3-(1-Benzimidazolyl)quinoline to HeterocyclotetraaromaticsThe monolithium derivatives of the title compounds 1a and 4 react with themselves giving macrocyclic addition products. Hydrolysis and oxidation of these products yield the heterocyclotetraaromatics diimidazo[1′,2′:1,8;2″,1″:4,5][1,5]diazocino[3,2-b:7,6-b']diquinoline (3a, 55%) and bisbenzimidazo[1′,2′:1,8;2″,1″:4,5][1,5]diazocino[3,2-b:7,6-b']diquinoline (5, 3%; by addition of NiF2 15%). - 3-(1-Pyrazolyl)quinoline (7) is distinctly more electrophilic against n-butyllithium than quinoline.
Notes:
Die Monolithium-Derivate der Titelverbindungen 1a und 4 reagieren zu makrocyclischen Selbstadditionsprodukten. Durch Hydrolyse und Oxidation entstehen daraus die racemischen Heterocyclotetraaromaten Diimidazo[1′,2′:1,8; 2″,1″:4,5][1,5]diazocino[3,2-b:7,6-b']dichinolin (3a, 55%) und Bisbenzimidazo[1′,2′:1,8;2″,1″:4,5][1,5]diazocino[3,2-b:7,6-b']dichinolin (5, 3%; bei NiF2-Zusatz 15%). - 3-(1-Pyrazolyl)chinolin (7) ist gegenüber n-Butyllithium deutlich elektrophiler als Chinolin.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19821150207
Permalink