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Palladium(0)-Cataly...
Palladium(0)-Catalyzed Synthesis of Spirocycles and Supercritical Chemistry using a Resistively Heated Flow Reactor
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- Adeyemi, Ahmed, 1986- (författare)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi,Preparative Medicinal Chemistry
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- Larhed, Mats, Professor (preses)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi,Plattformen för preklinisk PET,Science for Life Laboratory, SciLifeLab,Avdelningen för Molekylär Avbildning,Preparativ läkemedelskemi,Theranostics
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- Odell, Luke R., Associate Professor (preses)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi,Preparativ läkemedelskemi
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- Wärnmark, Kenneth, Professor (opponent)
- Centre for Analysis and Synthesis, Lund University
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(creator_code:org_t)
- ISBN 9789151308555
- Uppsala : Acta Universitatis Upsaliensis, 2020
- Engelska 93 s.
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Serie: Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy, 1651-6192 ; 283
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Abstract
Ämnesord
Stäng
- This doctoral thesis focusses on an effective and selective approach to the synthesis of spirocycles using palladium(0)-catalyzed Mizoroki-Heck reactions. In addition, selective and efficient chemistry was highlighted by the design and evaluation of a novel resistively heated system for continuous flow (CF) synthesis for high-temperature and high-pressure applications.Paper I described the design and evaluation of a novel resistively heated CF system. The design of a low-cost, simple, robust, and effective CF system involving a resistively heated steel reactor capable of delivering 400 °C and 200 bar was reported. The reactor was evaluated with esterification, transesterification and direct carboxylic acid to nitrile conversions using supercritical ethanol, methanol and acetonitrile respectively. Diels-Alder reactions under neat conditions were also carried out at high temperature and pressure.Paper II reported the synthesis of spirooxindoles by a selective application of the palladium(0)-catalyzed Mizoroki-Heck spirocyclization. The precursors for the reaction were synthesized by coupling 2-iodoanilines with esters derived from enantiomerically pure (+)-Vince lactam decorated with the bulky, directing 2,5-dimethylpyrrole protecting group. Ten different spirooxindoles were reported with good yields and high regio- and stereoselectivity. Functionalization of a synthesized spirooxindole was done by a palladium(0)-catalyzed alkoxycarbonylation, followed by selective deprotections.In Paper III, ether precursors were synthesized from (+)-Vince lactam, via a Mitsunobu reaction with the corresponding iodophenols. The precursors were later subjected to conditions for intramolecular Mizoroki-Heck reaction. Overall, 12 spiroethers were synthesized in useable yields, regioselectivity up to 98% and with excellent diastereoselectivity (d.e.>98%). Further functionalization to mono-protected rigidified amino acids was also demonstrated.
Ämnesord
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Farmaceutiska vetenskaper (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Pharmaceutical Sciences (hsv//eng)
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Läkemedelskemi (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Medicinal Chemistry (hsv//eng)
Nyckelord
- Continuous Flow
- Resistive heating
- Supercritical fluids
- high-temperature synthesis
- Mizoroki-Heck reaction
- Spirooxindoles
- Spiroethers
- Spirobenzofuranes
- Unnatural Amino Acids
Publikations- och innehållstyp
- vet (ämneskategori)
- dok (ämneskategori)
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