Boyko V. Regio- and stereoselective functionalization of calix[4]arenes

Українська версія

Thesis for the degree of Doctor of Science (DSc)

State registration number

0508U000410

Applicant for

Specialization

  • 02.00.03 - Органічна хімія

19-06-2008

Specialized Academic Board

Д 26.217.01

Institute of Organic Chemistry NAS of Ukraine

Essay

. The dissertation is dedicated to development of new methods of regio- and stereoselective functionalization of calix[4]arenes, their application for synthesis of inherently chiral calixarenes, investigation of influence of the intramolecular hydrogen bond in this processes, physico-chemical studies as well as influence on the biological processes of the obtaining compounds. The analysis of all possible stereo isomers of calix[4]arenes was made and two approaches to the synthesis of asymmetricaly substituted calix[4]arenes was suggested. For their realization the new methods of regioselective functionalization (alkylation, acylation, sulfonylation) were developed. The elaborating methods of selective functionalization were used for synthesis of inherentlychiral calixarenes whose chirality originates from the acymmetric arrangements of different groups to the lower or upper rims of the macrocycles. It was shown that calixarenes possessing sulfonylamidine, amide and aminophosphonic groups effectively inhibited calcium and sodium pumps of the smooth muscle cells.

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