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Synthesis of the First Heteroannularly Substituted Ferrocene Amino Acid and Isomeric Carbamic Acid Derivatives Containing Chiral Centres

Mojca Čakić Semenčić
Maja Dropučić
Lidija Barišić
Vladimir Rapić

Puni tekst: engleski, pdf (195 KB) str. 599-612 preuzimanja: 2.456* citiraj
APA 6th Edition
Čakić Semenčić, M., Dropučić, M., Barišić, L. i Rapić, V. (2006). Synthesis of the First Heteroannularly Substituted Ferrocene Amino Acid and Isomeric Carbamic Acid Derivatives Containing Chiral Centres. Croatica Chemica Acta, 79 (4), 599-612. Preuzeto s https://hrcak.srce.hr/5806
MLA 8th Edition
Čakić Semenčić, Mojca, et al. "Synthesis of the First Heteroannularly Substituted Ferrocene Amino Acid and Isomeric Carbamic Acid Derivatives Containing Chiral Centres." Croatica Chemica Acta, vol. 79, br. 4, 2006, str. 599-612. https://hrcak.srce.hr/5806. Citirano 07.12.2019.
Chicago 17th Edition
Čakić Semenčić, Mojca, Maja Dropučić, Lidija Barišić i Vladimir Rapić. "Synthesis of the First Heteroannularly Substituted Ferrocene Amino Acid and Isomeric Carbamic Acid Derivatives Containing Chiral Centres." Croatica Chemica Acta 79, br. 4 (2006): 599-612. https://hrcak.srce.hr/5806
Harvard
Čakić Semenčić, M., et al. (2006). 'Synthesis of the First Heteroannularly Substituted Ferrocene Amino Acid and Isomeric Carbamic Acid Derivatives Containing Chiral Centres', Croatica Chemica Acta, 79(4), str. 599-612. Preuzeto s: https://hrcak.srce.hr/5806 (Datum pristupa: 07.12.2019.)
Vancouver
Čakić Semenčić M, Dropučić M, Barišić L, Rapić V. Synthesis of the First Heteroannularly Substituted Ferrocene Amino Acid and Isomeric Carbamic Acid Derivatives Containing Chiral Centres. Croatica Chemica Acta [Internet]. 2006 [pristupljeno 07.12.2019.];79(4):599-612. Dostupno na: https://hrcak.srce.hr/5806
IEEE
M. Čakić Semenčić, M. Dropučić, L. Barišić i V. Rapić, "Synthesis of the First Heteroannularly Substituted Ferrocene Amino Acid and Isomeric Carbamic Acid Derivatives Containing Chiral Centres", Croatica Chemica Acta, vol.79, br. 4, str. 599-612, 2006. [Online]. Dostupno na: https://hrcak.srce.hr/5806. [Citirano: 07.12.2019.]

Sažetak
Syntheses of N- and C-protected derivatives of 1'-(1-aminoethyl)ferrocene-1-carboxylic acid (Fcca) and isomeric carbamic acid are reported. The first attempt to prepare N-Ac-Fcca (8) by cleavage of 1-[1-(acetamido)ethyl]-1'-(o-chlorobenzoyl)ferrocene (7) with t-BuOK/H2O/GLYME failed. Friedel-Crafts reactions of N-substituted (1-ferrocenylethyl)amines [Boc-Fea (5) and Ac-Fea (6)] with ClCOSMe/AlCl3 gave the corresponding heteroannularly substituted thioesters 9/10, which were hydrolyzed into Boc-Fcca/Ac-Fcca and esterified into Boc-Fcca-OMe (11)/ Ac-Fcca-OMe (12). In a multi-step sequence, bromoferrocene was transformed into 1’- brominated Fea (15), Boc-Fea (16) and Ac-Fea (17). Lithiation/ethoxycarbonylation of these bromine compounds gave the corresponding carbamic esters 18 and 19, instead of the expected Fcca esters. By lithiation/carboxylation and subsequent esterification, 5, 6, 16 and 17 were converted into the desired 11 and 12. 1'-Acetylferrocene-1-carboxylic acid (21) was transformed into oxime 22 and oxime-ester 23. Hydrogenation of this intermediate resulted in formation of Fcca-OMe (24) in very good yield. The structure of the compounds prepared was confirmed by HRMS and spectroscopic analyses.

Ključne riječi
ferrocene chiral amino acid; ferrocene chiral carbamic acid; oxime reduction; lithiation; carboxylation

Hrčak ID: 5806

URI
https://hrcak.srce.hr/5806

Posjeta: 2.805 *