Priprava višesupstituiranih indena i spiroindena

master's thesis

• Title (english): Synthesis of multisupstituted indenes and spiroindenes
• Author: David Šterpin
• Mentor: Nikola Topolovčan (mentor)
• Committee member: Đani Škalamera (predsjednik povjerenstva)
• Committee member: Iva Juranović Cindrić (član povjerenstva)
• Committee member: Biserka Prugovečki (član povjerenstva)
• Committee member: Željka Car (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2022-12-16, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru ovog diplomskog rada opisana je regioselektivna i kemoselektivna sinteza
višesupstituiranih indena i spiroindena u nekoliko sintetskih koraka počevši od komercijalno
dostupnih karbonilnih spojeva: benzofenona, 9-fluorenona i ftalimida. Sintetski put uključuje
adiciju acetilida na odgovarajući karbonilni spoj pri čemu su dobiveni propargilni alkoholi
prevedeni u željene produkte u sekvencijskim reakcijama Meyer-Schusterove pregradnje,
funkcionalizacije dobivenih enona u alilne alkohole te intramolekulske Friedel-Craftsove
alkilacije (Nazarov tip ciklizacije) u odgovarajući inden s naglaskom na kemoselektivnost i
regioselektivnost reakcije ciklizacije. Također je provedena kemoselektivna i regioselektivna
dvokomponentna reakcija između propargilnih alkohola i aromatskih nukleofila u svrhu
priprave spiroindena. Strukture pripravljenih spojeva potvrđene su analitičkim tehnikama i
postupcima (NMR, MS).

Abstract (english)

In this diploma thesis, regioselective and chemoselective synthesis of highly substituted indenes
and spiroindenes starting from commercially available carbonyl compounds (benzophenone, 9-
fluorenone and phtalimide) is described. Synthesis involves nucleophilic addition of various
acetylenes, Meyer-Schuster rearragement of the prepared propargylic alcohols followed by the
transformation of the corresponding enones to allylic alcohols, and finally Friedel-Crafts
reaction of the allylic alcohols to afford the corresponding indenes. Furthermore, a
regioselective and chemoselective two-component reaction of propargylic alcohols and
nucleophilic aromatic compounds affording spiroindenes is described. Structures of all
prepared compounds were confirmed by analytical techniques and procedures (NMR, MS).

• Keywords: Brønstedova kiselina; intramolekulska Friedel-Craftsova alkilacija; MeyerSchusterova pregradnja; spiroindeni; višesupstituirani indeni
• Keywords (english): Brønsted acid; intramolecular Friedel-Crafts alkylation; Meyer-Schuster rearrangement; multisubstituted indenes; spiroindenes
• Language: croatian
• URN:NBN: urn:nbn:hr:217:720640
• Project: Number: IP-2018-01-4053; Title: Nove strategije za pripravu tetrasupstituiranih kiralnih centara: asimetrične katalitičke reakcije usmjerene protuanionom; Acronym: NSYNC-ACDC; Leader: Matija Gredičak; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• 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: 2023-06-16
• Created on: 2023-01-13 09:30:06