Synthesis and structure of novel ferrocene-containing β-carbolines including polycondensed derivatives with the elements of planar-, central- and conformational chirality

Kovács, Zoltán and Jernei, Tamás and Katona, D. and Kocsis, László and Csámpai, Antal (2015) Synthesis and structure of novel ferrocene-containing β-carbolines including polycondensed derivatives with the elements of planar-, central- and conformational chirality. Journal of Organometallic Chemistry, 794. pp. 125-135. ISSN 0022-328X

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Abstract

Employing tryptamine or tryptophane methylester hydrochloride and (Sp)-2-formylferrocene-1- carboxylate as precursors by means of PicteteSpengler reactions and subsequent intramolecular acylation effected by cyanuricfluoride or carbonyldiimidazole (CDI), the first representatives of ferrocenecontaining b-carboline derivatives including polycyclic ferroceno/fused lactames, were prepared. In the course of CDI-mediated tandem cyclization of a tryptophane-derived carboxyferrocenyl-substituted bcarboline, a ring enlargement simultaneously taking place with the loss of the h5-C5H5Feþ fragment of the fused ferrocene moiety, effected by the coordinating imidazole released from the reagent, led to a 4Hcyclopenta[ 7,8]azonino[5,4-b]indole as a minor product. The constitution and relative configuration of the new compounds with the elements of planar-, central- and conformational chirality were established by NMR methods including HMQC, HMBC and NOESY measurements supported by DFT modeling studies.

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