Konstantina Koriatopoulou, N. Karousis, G. Varvounis
Oct 13, 2008
Citations
1
Influential Citations
23
Citations
Journal
Tetrahedron
Abstract
Abstract A novel four-step synthesis to the pyrrolo[2,1- c ][1,4]benzodiazocine ring system is described. 1 H -Pyrrole-2-carbaldehyde was alkylated with ethyl or methyl bromoacetate and the resulting ethyl or methyl (2-formyl-1 H -pyrrol-1-yl)acetates oxidised with potassium permanganate to the corresponding 1-[(2-ethoxy or methoxy)-2-oxoethyl]-1 H -pyrrole-2-carboxylic acids. The latter was converted into their acid chlorides by reaction with thionyl chloride and without isolation transformed into the respective methyl 2-({[1-(2-ethoxy or methoxy-2-oxoethyl)-1 H -pyrrol-2-yl]carbonyl}amino)benzoates by reaction with methyl anthranilate. Dieckmann condensation of methyl 2-({[1-(2-methoxy-2-oxoethyl)-1 H -pyrrol-2-yl]carbonyl}amino)benzoate provided the pyrrolo[2,1- c ][1,4]benzodiazocine.