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Development of novel methodologies for the syntheses of biologically relevant nitrogen-heterocycles
Roy, Sudipta (2014) Development of novel methodologies for the syntheses of biologically relevant nitrogen-heterocycles. PhD, Universität Regensburg.Date of publication of this fulltext: 16 Jan 2014 17:15
Thesis of the University of Regensburg
DOI to cite this document: 10.5283/epub.27175
Abstract (English)
Nitrogen containing heterocyclic compounds are wide spread and common structural scaffold in many natural products. Moreover these molecules received huge importance for their medicinal and pharmaceutical uses. N-heterocycles very frequently contain multiple stereocenters. Several synthetic methodologies were developed. Among them multicomponent microwave irradiated organization of starting ...
Nitrogen containing heterocyclic compounds are wide spread and common structural scaffold in many natural products. Moreover these molecules received huge importance for their medicinal and pharmaceutical uses. N-heterocycles very frequently contain multiple stereocenters. Several synthetic methodologies were developed. Among them multicomponent microwave irradiated organization of starting substrates into a targeted N-heterocyles has more advantage over the multi step synthesis due to the time and labor economic reasons. Regio- and stereo-selective synthesis of cyclopropane containing tetrahydropyrroloquinoline derivatives were synthesized following well established Povarov reaction. In this Ph.D work recent developments on Povarov reactions were discussed and utilizing this reaction as a key step how other N-heterocycles were synthesized in regio- and steroselective manner was discussed. Either utilizing Povarov reaction as a key step quinoline substituted cis-4,5-disubstituted pyrrolidinone was synthesized exclusively. Tetryhydro-, dihydro- and 1H-pyrazoles were also synthesized replacing aniline by monosubstituted hydrazine in multicomponent Povarov reaction.
Translation of the abstract (German)
Stickstoff-Heterozyklen sind ein häufig anzutreffender Strukturbaustein vieler Naturstoffe. Weiterhin besitzen diese Moleküle eine große Bedeutung auf Grund ihrer medizinischen und pharmazeutischen Anwendung. N-Heterozyklen enthalten häufig mehrere stereogene Zentren. Diverse synthetische Methoden wurden entwickelt. Hierbei besitzt die Multikomponenten Synthese unter Nutzung von ...
Stickstoff-Heterozyklen sind ein häufig anzutreffender Strukturbaustein vieler Naturstoffe. Weiterhin besitzen diese Moleküle eine große Bedeutung auf Grund ihrer medizinischen und pharmazeutischen Anwendung. N-Heterozyklen enthalten häufig mehrere stereogene Zentren. Diverse synthetische Methoden wurden entwickelt. Hierbei besitzt die Multikomponenten Synthese unter Nutzung von Mikrowellenstrahlung gegenüber der herkömmlichen mehrstufigen Synthese ökonomische und auf die Arbeitszeit bezogene Vorteile. Regio- und stereoselektive Synthese von Cyclopropan enthaltenen Tetrahydropyrrolochinolin-Derivaten gelang über die etablierte Povarov-Reaktion. In dieser Doktorarbeit werden aktuelle Entwicklungen der Povarov-Reaktion diskutiert, wobei diese Reaktion den Schlüsselschritt für die regio- und stereoselektive Synthese andere N-Heterozyklen diente. Hierbei wurden selektiv nur cis-4,5-disubstituierte Pyrrolidinone erhalten. Tetrahydro-, Dihydro- und 1H-Pyrazole wurden ebenfalls synthetisiert durch Austausch von Anilin durch monosubstituierte Hydrazine mittels einer Multikomponenten Povarov Reaktion.
Involved Institutions
Details
| Item type | Thesis of the University of Regensburg (PhD) |
| Open Access Type: | Primary Publication |
|---|---|
| Date | 8 January 2014 |
| Referee | Prof. Dr. Oliver Reiser |
| Date of exam | 17 December 2012 |
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Keywords | Catalytic multicomponent reactions, tetrahydroquinolines, pyrrolidinones, pyrazoles |
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences |
| Status | Published |
| Refereed | Yes, this version has been refereed |
| Created at the University of Regensburg | Yes |
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-271751 |
| Item ID | 27175 |
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