Smolii O. Functionalized Phosphonium Ylides in Syntheses of Bioactive Derivatives of Nitrogen Containing Heterocycles

Українська версія

Thesis for the degree of Doctor of Science (DSc)

State registration number

0506U000302

Applicant for

Specialization

  • 02.00.10 - Біоорганічна хімія

26-05-2005

Specialized Academic Board

Д 26.220.01

V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine

Essay

Phosphonium reagents for the heterocyclization. Development of directions of application of functionalized phosphonium ylides in the syntheses of bioactive derivative of nitrogenous heterocycles. Chemical synthesis, ІR-, UV- and PMR-spectroscopy, quantum-chemical computations. On the development of phosphonium syntheses of new types of substituted azoles, azines, azoloazines with biophoric groups containing sulphur and phosphorus, it was shown that of fundamental importance in syntheses of this kind are modifications of the phosphonium ylides by reactions with 1,2,2,2-tetrachloroethylisocyanate, acylisothiocyanates and other multicenter electrophilic agents. Convenient methods for preparation of a number of new derivatives of oxazole, thiazole, pyrazole, s-tri-azole, pyrimido[1,6-a]benzimidazole, pyrazolo[1,5-a]pyrimidine and s-triazolo[1,5-a]-pyrimidine were developed on the basis of the modified phosphonium ylides. Of particular interest were phosphonium syntheses of new 4-amino-6-mercapto- and 4,6-dimercapto-pyrimidine derivatives as well as acyclonucleosides based on these compounds. It was shown that some derivatives are highly effective antiseptics and are worthy of further consideration.Sphere of the use - bioorganic chemistry, organic chemistry.

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