SYNTHESIS OF CARBAZOLE DERIVATIVES .1. REACTION OF 3-(2-NITROETHENYL)-INDOLE-2-MALONIC ACID-ESTERS WITH MICHAEL-ACCEPTORS

MAHBOOBI, S and BURGEMEISTER, T and KASTNER, F (1995) SYNTHESIS OF CARBAZOLE DERIVATIVES .1. REACTION OF 3-(2-NITROETHENYL)-INDOLE-2-MALONIC ACID-ESTERS WITH MICHAEL-ACCEPTORS. ARCHIV DER PHARMAZIE, 328 (1). pp. 29-38. ISSN 0365-6233,

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Abstract

Michael-type reactions 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

Item Type: Article
Uncontrolled Keywords: DIELS-ALDER REACTIONS; INDUSTRIAL SYNTHESIS; ELLIPTICINE SERIES; INDOLES; ALKALOIDS; VINYLINDOLES; ACCESS;
Depositing User: Dr. Gernot Deinzer
Last Modified: 19 Oct 2022 08:38
URI: https://pred.uni-regensburg.de/id/eprint/52816

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