Unit:
Κατεύθυνση Οργανική Σύνθεση και Εφαρμογές της στη Χημική ΒιομηχανίαLibrary of the School of Science
Supervisors info:
Αθανάσιος Γκιμήσης, Καθηγητής Τμήμα Χημείας ΕΚΠΑ
Βικτωρία Μαγκριώτη, Αναπληρώτρια Καθηγήτρια Τμήμα Χημείας ΕΚΠΑ
Γιώργος Βουγιουκαλάκης, Αναπληρωτής Καθηγητής Τμήμα Χημείας ΕΚΠΑ
Original Title:
Μελέτη Μηχανισμού Σχηματισμού Ν3-Υποκατεστημένων 2Η-Πυριδο-[1,2,α][1,3,5]-τριαζινο-2,4-(3Η)-διονών και Ανάπτυξη Πρωτοκόλλων Σύνθεσης Ν4-Αρυλο-Ν1-(β-D-γλυκοπυρανοζυλο)κυτοσινών.
Translated title:
Μελέτη Μηχανισμού Σχηματισμού Ν3-Υποκατεστημένων 2Η-Πυριδο-[1,2,α][1,3,5]-τριαζινο-2,4-(3Η)-διονών και Ανάπτυξη Πρωτοκόλλων Σύνθεσης Ν4-Αρυλο-Ν1-(β-D-γλυκοπυρανοζυλο)κυτοσινών.
Summary:
The first part of this master thesis deals with the investigation of the possible mechanism of formation of 2H-pyrido-[1,2,α]-[1,3,5]-triazino-2,4-(3H)-diones through the reaction of N-(hydroxycarbamoyl) derivatives of amino acids in the presence of triphosgene and pyridine. For this purpose, the methoxycarbamoyl derivative of ethyl glycinate was synthesized and allowed to react under the above conditions, leading to a new product that was fully characterized. Furthermore the synthesis of a hydroxycarbamoyl derivative of a secondary amine (morpholine) was performed and the product was subjected to the same conditions in an attempt to isolate a key postulated intermediate of the proposed mechanism. The above experiments provided evidence that aided the clarification of the reaction mechanism.
In the second part of the present thesis, two new protocols were applied to the synthesis of N4-aryl-N1-(β-D-glucopyranosyl)-cytosines, as potential inhibitors for the catalytic site of glycogen phosphorylase. In Method A, the synthesis of the target compounds is based, on the key step, on a Buchwald-Hartwig-type reaction of acetyl-protected β-D-glucopyranosylcytosine with aryl iodides in the presence of a Palladium catalyst. In Method B, protic acid conditions are used and specifically, in the presence of pivalic acid, a substitution reaction of 4-(1,2,4-triazol-1-yl) pyrimidine derivatives from arylamines takes place. The above experiments helped to expand the application of the two methods with new substrates and gave useful conclusions on the scope of each method.
Main subject category:
Science
Keywords:
Ιnhibitors, glycogen phosphorylase, isatin, Βuchwald-Hartwig reaction, 2H-pyrido-[1,2-α]-[1,3,5]-triazin-2,4-(3Η)–dione.
Number of references:
115
