10 H-INDOLO[3,2-B]QUINOLINE-5-OXIDE (OXYQ UINDOLINE) AND SOME OF ITS DERIVATIVES

The experiments of Rudolf Boehringer's philosophical doctorate (1907) have been repeated, methodically varied and the structure of the produ cts has been proved by spectroscopic methods. The alkoxyindole 10b obt ained from the dioxyquindoline (7) and ethyl bromoacetate was treated with triethylamine to yield the title-compound ga. The N-oxide 12 rece ived from 10a reacts with ethanolate to give the vinylogous hydroxamic acid 13. The transformation of 8a to the quindolinone 3a is described . Compound 8a has been submitted to nitration with following reduction , acetylating reactions, methylation and halogenation. The 11-thio and the 11-alkoxy-quindolines have been synthesized from the 11-chloroqui ndolines 23 and the quindolinones 3.