[Synthesis of carbazole derivatives. 1. The reaction of 3-(2-nitroethenyl)-indole-2-malonic acid esters with Michael acceptors].
Michael-type reaction of compounds of type 9 were studied. Addition reactions with acrolein and methyl vinyl ketone, respectively, lead--depending on the conditions--to pyridoindoles of type 16 and 14 and/or to tetrahydrocarbazoles of type 17 and 15. With Triton B compounds 15 undergo retro-Michael-type elimination of the nitromethyl group, followed by hydrolysis/decarboxylation and dehydrogenation, leading to the disubstituted carbazoles 20. In the case of 17a, the primary elimination product 18 could be isolated. The synthetic potential of these reaction types is discussed. Some of the described compounds and derivatives of them show antimycobacterial activity.
Mahboobi
S
S
Institut für Pharmazie, Universität Regensburg.
Burgemeister
T
T
Kastner
F
F
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D008314:Malonates / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D009161:Mycobacterium / Q000187:drug effects
D000900:Anti-Bacterial Agents; D008314:Malonates