Naslov
Preparation of ferrocene heteroannularly substituted amino acids, their precursors and derivatives

Autori
Rapić, Vladimir ; Barišić, Lidija ; Zorić, Zoran

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
XIIIth FECHEM Conference on Organometallic Chemistry 1999 / Dias, Alberto Romao ; Garcia, M. Helena - Lisabon : Sociedade Portuguesa de Química, 1999, 294-294

Skup
XIIIth FECHEM Conference on Organometallic Chemistry 1999

Mjesto i datum
Lisabon, Portugal, 29.08.1999. - 03.09.1999

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
ferrocene; ferrocene-containing amines; ferrocene heteroannularly substituted amino acids

Sažetak
In continuation of our studies in the field of ferrocene-containing amines, oligoamides and amino acids 1 (R=H, Me; m=0-3; n=1-9) (Z.Zorić, V. Rapić, S. Lisac, M. Jukić, J. Polymer Sci., Part A: Polymer Chemistry 37 (1999) 25-36) we decided to prepare and investigate some new types of ferrocene heteroannularly substituted amino acids 2 (R=H; m, n=0-3). These compounds and/ or their precursors and derivatives were obtained by multistep syntheses starting from 1, 1'-diacetylferrocene, N, N, N-trimethylferrocenyl-methylammonium iodide, or methyl ferrocenealkanoates. E. g. , oxidation of 1, 1'-diacetylferrocene with bromine in dioxane gave ferrocene-1, 1'-dicarboxylic acid. Its dimethyl ester was partially hydrolyzed to monoester, which was converted to ester-azide. Curtius rearrangement of this azide in the presence of acetic anhydride gave the desired 1'-aminoferrocenecarboxylic acid (2, m=n=0) via intermediate acetamide. The action of pottasium cyanide on N, N, N-trimethylferrocenylmethylammonium iodide gave ferroceneacetonitrile, which was hydrolyzed to ferroceneacetic acid. The corresponding methyl ester was acylated to methyl 1'-acetylferroceneacetate, which was selectively reduced to ester-carbinol. By condensation of this compound with mercaptoacetic acid in the presence of TFA in dichloromethane, thiaacid HOOCCH_2CH_10FeCH(CH_3)SCH_2COOH was obtained. The cleavage of this aminoacid precursor to 2 (R=Me, m=n=1) in standard way (by NH_3/ NH_4Cl/ HgCl_2) was unsuccessful. The amino acids prepared were characterized as the corresponding esters and N-acyl derivatives. By means of spectroscopic analysis and on the basis of other physical properties it was demonstrated that these compounds exist in the expected zwitterionic form. The unsuccessful conversion of thiaacidic precursors to the corresponding amino acids 2 (n=1) will be discussed.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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