Novel one-pot multi-reaction methods for the synthesis of carbocyclic and heterocyclic compounds

QD Chemistry

Faggyas, Réka Julianna ; Sutherland, Andrew

University:University of Glasgow

Department:School of Chemistry

关键词: One-pot reactions, Multistep reactions, Tandem catalysis, Transition metal catalysis, Palladium catalysis, Indanols, Diazotisation, Quinolones, Benzotriazoles.;   

Others  :  http://theses.gla.ac.uk/75136/1/2019faggyasphd.pdf

来源: University of Glasgow

【 摘 要 】

The first section describes the development of an asymmetric one-pot synthesis of 1-alkylindan-1-ols involving an enantioselective allylboration of 2’-bromoaryl alkyl ketones followed by an intramolecular Mizoroki-Heck cyclisation. The synthetic utility of the chiral 1-alkylindan-1-ol scaffold was demonstrated using the ozonolysis product indanone in diastereoselective reductive reactions. The second section describes the development of a rapid, one-pot tandem diazotisation and Heck-Matsuda reaction for the synthesis of methyl (E)-cinnamates via stable aryl diazonium tosylate salts. This process was then altered to allow the one-pot multistep synthesis of 3,4-dihydroquinolin-2-ones. This methodology was used for the total synthesis of a sodium channel modulator. The third section describes a one-pot diazotisation-intramolecular cyclisation process for the synthesis of 1H-benzotriazoles and the regioselective preparation of N1-substituted benzotriazoles, including a series of biologically active compounds.