Synthesis of fluoroalkenyl uracil, precursors : NMR characterization of organofluorine lanthanide compounds

Keywords

Organofluorine compounds

Abstract

I. Fluoroalkenyl uracil derivatives are compounds with excellent potential to be used as antiviral or anticancer agents. A multi-step synthesis was designed (Scheme I) which involves the condensation of urea and its derivatives (2a, b) with diethyl allylmalonate (1), and the radical addition of dibromodifluoromethane. Treatment with phosphorus oxychloride to give chlorouracils (5a, b) is followed by double dehydrobromination to synthesize 5-(4, 4-difluorobutadienyl)chlorouracils (6a, b). Further reduction will produce 5-(4, 4-difluorobutadienyl)uracils (7a, b). 5-Allylbarbituric acid derivatives (3a, b) have been isolated and the transformation into 5-(2, 4-dibromo-4, 4difluorobutyl) barbituric acids ( 4a, b) was attempted as a building block for the synthesis of 5-(4, 4-difluorobutadienyl)uracils. II. The focus of this report is the NMR characterization of organofluorinated lanthanide compounds as a way to gain insight into structure and bonding properties while generating physical data that can serve in the future for identification of similar compounds. Nine lanthanide compounds bearing organofluorine ligands were studied by proton, carbon13 and fluorine-19 NMR. The lanthanides studied were: praseodymium (Pr), neodymium (Nd), gadolinium (Gd), dysprosium (Dy) and ytterbium (Yb). The organofluorine ligands used in this study were: trifluoroacetate, pentafluoropropionate and heptafluorobutyrate. II Other ligands like 2-bromopropionate and bis(trimethylsilyl)amide were used for companson.

Notes

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Graduation Date

2002

Advisor

Elsheimer, Seth

Degree

Master of Science (M.S.)

College

College of Arts and Sciences

Department

Chemistry

Format

PDF

Pages

78 p.

Language

English

Length of Campus-only Access

None

Access Status

Masters Thesis (Open Access)

Identifier

DP0028719

Subjects

Arts and Sciences -- Dissertations, Academic; Dissertations, Academic -- Arts and Sciences

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