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Identifier

000428509

Title

Methylene blue catalysed oxidation of 2-oxindoles to isatins and photocatalysed reductive cyclization of 2-enones

Alternative Title

Καταλυόμενη από μπλε του μεθυλενίου οξείδωση 2-οξινδολίων σε ισατίνες και φωτοκαταλυόμενη αναγωγική κυκλοποίηση 2-ενονών

Author

Σφακιανάκη, Καλλιόπη Π.

Thesis advisor

Βασιλικογιαννάκης, Γεώργιος

Reviewer

Κατερινόπουλος, Χαράλαμπος
Στρατάκης, Μανώλης

Abstract

In Chapter 1, a methodology for synthesizing 3-hydroxy-2-oxindoles and isatins is described. These compounds exhibit a variety of biological properties and constitute valuable scaffolds in organic synthesis. For the synthesis of these structures, 2- oxindoles were subjected to reaction’s conditions, which included MeOH as a solvent, methylene blue as a radical initiator and molecular oxygen as oxidant. In total, 9 oxidized derivatives of 2-oxindoles were synthesized in only one stage and in very good yields. In Chapter 2, the synthesis of substituted cyclopentanes, starting from 2-enones, is presented. An EtOH solution of 2-enones, containing also Hantzsch ester (HE), DIPEA and eosin Y was irradiated with visible light to afford the corresponding cyclopentane. The scope and the limitations of the methodology are under investigation. Finally, a new synthetic methodology for the reduction of the double bond of 2,3-unsaturated 1,4-diketones was developed. The formation of the unsaturated 1,4- diketone was achieved by oxidation of a furan, followed by addition of Me2S. Subsequently, the 2,3-unsaturated 1,4-diketone was irradiated, according to the method mentioned above, and afforded the corresponding saturated 1,4-diketone.

Language

English, Greek

Subject

1,4-diketones

1,4-δικετόνες

2- ενόνες

3-hydroxy-2-oxindoles

3-υδροξυ-2-οξινδόλια

Cyclopentanes

Eosin Y

Hantzsch ester

Oxygen