Unit:
Κατεύθυνση Οργανική Σύνθεση και Εφαρμογές της στη Χημική ΒιομηχανίαLibrary of the School of Science
Author:
Apostolidi Eugenia-Maria
Supervisors info:
Επιβλέπων Καθηγητής : Μηνακάκη-Μουτεβελή Παναγιώτα, Καθηγήτρια ΕΚΠΑ
Γεωργιάδης Δημήτριος, Αναπληρωτής Καθηγητής ΕΚΠΑ
Μαγκριώτη Βικτώρια, Αναπληρώτρια Καθηγήτρια, ΕΚΠΑ
Original Title:
ΕΚΛΕΚΤΙΚΗ ΑΠΟΠΡΟΣΤΑΣΙΑ Ν-BOC ΕΤΕΡΟΚΥΚΛΙΚΩΝ ΔΑΚΤΥΛΙΩΝ ΚΑΙ ΑΝΑΠΤΥΞΗ ΝΕΑΣ ΜΕΘΟΔΟΛΟΓΙΑΣ ΓΙΑ ΤΗ ΣΥΝΘΕΣΗ ΔΙΥΔΡΟΠΥΡΙΜΙΔΙΝΟ-4,6 (1Η, 5Η)-ΔΙΟΝΩΝ
Translated title:
SELECTIVE REMOVAL OF N-BOC HETEROCYCLIC RINGS AND DEVELOPMENT OF A NEW METHODOLOGY FOR THE SYNTHESIS OF DIHYDROPYRIMIDIN-4,6 (1H, 5H) -DIONE DERIVATIVES
Summary:
In this project, two subjects were studied with the following results:
A simple method for the selective cleavage of the Ν-Boc protecting group from imidazole, benzimidazoles, pyrazole and their derivatives in good to excellent yields (75-98%) has been developed. It is worth noting that the present method does not lead to the cleavage of the Boc group from Boc- protected primary amines and from the Boc-protected heterocyclic compounds of indole and pyrrole. In addition, the knowledge of a possible deprotection of the Ν-Boc-heterocyclic rings (imidazole, benzimidazole and pyrazole) with the use of a widely-used reducing agent, such as NaBH4, we believe it is very useful in the case of a multistep synthesis of compounds with a variety of orthogonally protected functional groups because, if such reduction is attempted at a later stage in the synthetic process, it will result in complications from the deprotection of the aforementioned rings.
A new methodology is introduced for the synthesis of heterocyclic compounds of dihydropyrimidin-4,6 (1Η, 5Η)-dione (I) derivatives. According to this methodology, it will be possible to insert several groups, as well as, at least in theory, the side chains of the amino acids (R2) in the 2-position of the ring. Compound 23 was synthesized following the new synthetic process.
Main subject category:
Science
Keywords:
: tert-butoxycarbonyl group, deprotection, imidazole, pyrazole, pyrimidines
