Synthesis of Potentially Biologically Active Cyclopropane- and Spirocyclopropane-annelated Oligoazaheterocycles

Synthese von potentiellen biologischen aktiven cyclopropane- und spirocyclopropane-anellierten Oligoheterocyclen

by Martina Gensini
Doctoral thesis
Date of Examination:2003-01-30
Date of issue:2004-11-23
Advisor:Prof. Dr. Armin de Meijere
Referee:Prof. Dr. Armin de Meijere
Referee:Prof. Dr. Ulf Diederichsen
Persistent Address: http://dx.doi.org/10.53846/goediss-2102

 

 

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Abstract

English

In this work the synthesis of new cyclopropane- and spirocyclopropane-annelated heterocyclic compounds containing nitrogen has been reported. The Ti-mediated intramolecular reductive cyclopropanations of 2-allylamino-N,N-dialkylpropionamides were investigated towards the synthesis of 1-amino-3-azabicyclo[3.1.0]hexane and 1-amino-3-azabicyclo[4.1.0]heptane derivatives. Tri- and tetracyclic derivatives containing ring-annelated azabicyclo[3.1.0]hexane systems were prepared from indole, indoline, pyrrole and proline N-allyl derivatives by Ti-mediated intramolecular reductive cyclopropanations.In the second part of this thesis the 1,3-dipolar cycloaddition of various nitrones to the highly strained cyclopropylidenespiropentane and 7-cyclopropylidenedispiro[2.0.2.1]heptane and subsequent thermal rearrangement of the intermediate isoxazolidines was investigated. Such processes led to the formation of new tetrahydropyridone derivatives with up to three spirocyclopropane-annelated rings.
Keywords: metal complexes; catalysis; titanium; palladium; cycloadditions

Other Languages

In dieser Arbeit die Synthese von neuen cyclopropane- and spirocyclopropane-anellierten Heterocyclen wurde geschrieben. Die Intramoleculare Titan-vermittelte Cyclopropanierung von 2-allylamino-N,N-dialkylpropionamide wurde untersucht in der Synthese von 1-Amino-3-azabicyclo[3.1.0]hexane bzw. 1-Amino-3-azabicyclo[4.1.0]heptane Produkte. Tri- bzw. tetracyclen mit ring-anellierte Azabicyclo[3.1.0]hexane Systeme wurden synthetisiert von Indole, Indoline, Pyrrole and Proline N-allyl-Producte durch Intramoleculare Titan-vermittelte Cyclopropanierung.Im zweiten Teil der Arbeit die 1,3-dipolare Cycloadditione von verschiedene Nitronen mit Cyclopropylidenespiropentane and 7-cyclopropylidenedispiro[2.0.2.1]heptane und danach thermische Umlagerung von isoxazolidinen wurde untersucht. Diese Prozessen führten zu neuen Tetrahydropyridonederivaten mit spirocyclopropane-anellierte Ringe.
Schlagwörter: Metallkomplexe; Katalyse; Titan; Palladium; Cycloadditionen
 
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