Development of Organocatalitic Methodologies for the Synthesis of Bioactive Compounds

Doctoral Dissertation uoadl:1326322 679 Read counter

Unit:
Κατεύθυνση Οργανική Χημεία
Library of the School of Science
Deposit date:
2016-12-21
Year:
2016
Author:
Theodorou Alexiοs-Nikolaos
Dissertation committee:
ΧΡΙΣΤΟΦΟΡΟΣ ΚΟΚΟΤΟΣ, Επίκουρος Καθηγητής, Tμήμα Χημείας, ΕΚΠΑ
ΓΕΩΡΓΙΟΣ ΚΟΚΟΤΟΣ, Καθηγητής, Tμήμα Χημείας, ΕΚΠΑ
ΒΙΚΤΩΡΙΑ ΜΑΓΚΡΙΩΤΗ, Επίκουρη Καθηγήτρια, Tμήμα Χημείας, ΕΚΠΑ
ΠΑΝΑΓΙΩΤΑ ΜΟΥΤΕΒΕΛΗ-ΜΗΝΑΚΑΚΗ, Καθηγήτρια, Tμήμα Χημείας, ΕΚΠΑ
ΣΤΑΜΑΤΙΑ ΒΑΣΙΛΕΙΟΥ, Επίκουρη Καθηγήτρια, Tμήμα Χημείας, ΕΚΠΑ
ΓΕΩΡΓΙΟΣ ΒΟΥΓΙΟΥΚΑΛΑΚΗΣ, Επίκουρος Καθηγητής, Tμήμα Χημείας, ΕΚΠΑ
ΔΗΜΗΤΡΗΣ ΠΑΠΑΧΑΤΖΗΣ, Ερευνητής Α, Εθνικό Ίδρυμα Ερευνών
Original Title:
Ανάπτυξη Οργανοκαταλυτικών Μεθοδολογιών για τη Σύνθεση Βιοδραστικών Ενώσεων
Languages:
Greek
Translated title:
Development of Organocatalitic Methodologies for the Synthesis of Bioactive Compounds
Summary:
Organocatalysis constitutes a new, fast moving and expanding field in Organic Chemistry. In recent years, more efforts are made towards the use of mild and environmentally safe oxidants. The Organic Chemistry Laboratory of the National and Kapodistrian University of Athens has introduced an organocatalytic oxidation method, employing 2,2,2-trifluoromethyl acetophenone as the organocatalyst and hydrogen peroxide as the green oxidant. This thesis presents the expansion of this method in the introduction of one-pot reactions for the synthesis of high molecular complexity and useful compounds in Organic Synthesis. More specifically, we present:
• An one-pot synthesis of O-allylhydroxylamines through the organocatalytic oxidation of tertiary allylic amines followed by a [2,3]-Meisenheimer rearrangement
• The optimization ofthe reaction conditions for the selective oxidation of aniline to azoxybenzene or nitrobenzene.
• The synthesis of indolines, pyrrolidines, tetrahydrofurans, 2-oxazines and dihydro-oxazoles by epoxidation of olefins followed by ring closing reactions.
• The green dihydroxylation of olefins.
• The optimization of the reaction conditions for the synthesis of protected and non-protected α-hydroxy substituted ketones via the oxidation of silylenol ethers.

Furthermore, a general procedure for the synthesis of 2-oxoamides has been developed, aiming at the design and synthesis of new potential inhibitors of enzymes.
Main subject category:
Science
Other subject categories:
Organic chemistry
Keywords:
οrganocatalysis, oxidation, azoxy compounds, nitro compounds, indolines, pyrolidines, tetrahydrofurans, α-hydroxy ketones, oxazines, oxazoles, oxoamides
Index:
No
Number of index pages:
10
Contains images:
No
Number of references:
171
Number of pages:
215
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