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-... More 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). Less

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... More 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). Less

• 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