Priprava 9-O-karbamata cinhonidina i 10,11-dihidrocinhonidina

master's thesis

• Title (english): Preparation of 9-O-carbamates of cinchonidine and 10,11-dihydrocinchonidine
• Author: Ivona Kurečić
• Mentor: Ines Primožič (mentor)
• Committee member: Ines Primožič (predsjednik povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Biserka Prugovečki (član povjerenstva)
• Committee member: Đani Škalamera (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2020-09-25, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Ovim diplomskim radom pripravljen je 10,11-dihidrocinhonidin, njegovi karbamatni derivati
te karbamatni derivati cinhonidina. 10, 11-dihidrocinhonidin pripravljen je redukcijom vinilne
skupine cinhonidina korištenjem amonijevog formijata i ugljika na paladiju reakcijom
prijenosnog katalitičkog hidrogeniranja. Serija karbamatnih derivata pripravljena je reakcijom
alkaloida i odgovarajućeg izocijanata ili karbamoil-klorida. Korišteni su fenil- i
cikloheksilizocijanat kao i dietil-, difenil- i dimetilkarbamoil-klorid. Dobiveni su mono- i
disupstituirani alifatski te mono- i disupstituirani aromatski karbamatni derivati cinhonidina i
10,11-dihidrocinhonidina. Pripravljenim spojevima određeno je specifično optičko zakretanje
i talište, a karakterizirani su infracrvenom spektroskopijom te spektroskopijom nuklearne
magnetske rezonancije (1H i 13C).

Abstract (english)

In this diploma thesis synthesis of 10,11-dihydrocinchonidine, its carbamate derivatives and
carbamate derivatives of cinchonidine was described. 10,11-dihydrocinchonidine was
prepared by a transfer catalytic hydrogenation of cinchonidine over a palladium on carbon
catalyst using ammonium formate as hydrogen donor. A series of carbamate derivatives was
prepared in reaction of an alkaloid and the corresponding isocyanate or carbamoyl chloride.
Phenyl- and cyclohexyl- isocyanate were used as well as diethyl-, diphenyl- and
dimethylcarbamoyl chloride. Mono- and disubstituted aliphatic and mono- and disubstituted
aromatic cinchonidine carbamates and 10,11-dihydrocinchonidine carbamates have been
obtained. Optical rotation and melting point of synthesized compounds were determined.
Furthermore, synthesized compounds were analyzed by infrared and nuclear magnetic
resonance spectroscopy (1H and 13C).

• Keywords: alkaloid; cinhonidin; 10; 11-dihidrocinhonidin; karbamat; redukcija
• Keywords (english): alkaloid; cinchonidine; 10; 11-dihydrocinchonidine; carbamate; reduction
• Language: croatian
• URN:NBN: urn:nbn:hr:217:770674
• Study programme: Title: Graduate university studies in chemistry; specializations in: Research programme; Course: Research programme; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra kemije (magistar/magistra kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2022-09-25
• Created on: 2020-10-07 09:22:38