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Tesi etd-06052020-093731


Thesis type
Tesi di laurea magistrale LM5
Author
MONTAGNANI, ERIKA
URN
etd-06052020-093731
Title
Application of non convalent interactions: from autocatalysis to new dearomatization protocols.
Struttura
FARMACIA
Corso di studi
CHIMICA E TECNOLOGIA FARMACEUTICHE
Supervisors
relatore Prof. Pineschi, Mauro
relatore Prof.ssa Syusanna Harutyunyan
Parole chiave
  • dearomatization reaction
  • 1 4 Cu-catalyzed addition
  • autocatalysis
  • H-bonding
  • π-π stacking interaction
Data inizio appello
08/07/2020;
Consultabilità
Secretata d'ufficio
Data di rilascio
08/07/2090
Riassunto analitico
Non covalent interactions are of extreme relevance in various areas of biology and chemistry, namely structural biology, medicinal or supramolecular chemistry. For instance, their relevance become clear in the stabilization of DNA and protein structures as well as in the interaction drug- receptor.
In this thesis, non-covalent interactions are exploited as a strategic tool towards a novel autocatalytic [4+4] photodimerization reaction. Moreover, a new protocol for the dearomatization and subsequent functionalization of naphthol derivatives is presented.
In the first part of this thesis, the photodimerization of the azaanthracene is devised as a strategic reaction to investigate and develop a novel autocatalytic process. In this reaction a series of molecular linkers (organic compounds with hydrogen bond donor abilities) are going to be explored as key components to promote autocatalysis through intermolecular interactions. In the second part of this work, we have continued and expanded a study previously developed at the Harutyunyan group: the dearomatization of naphthol followed by the 1,4-addition of different nucleophiles. Specifically, it was reported that the Cu-catalyzed addition of diethyl zinc to an in situ dearomatized naphthol never exceeds a 50% yield. This result was assigned to the formation of aggregates between various units of naphthone derived from the dearomatization step. Based on this hypothesis, we propose to explore the addition of different complexating agents that can interact with the naphthone aggregates, through π–π stacking interactions, and induce disaggregation while promoting the reaction.

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