Synthesis of monosubstituted functional derivatives of carboranes from 1-mercapto-ortho-carborane: 1-HOOC(CH(2))(n)S-1,2-C(2)B(10)H(11) and [7-HOOC(CH(2))(n)S-7,8-C(2)B(9)H(11)](-) (n = 1-4).
A general approach to synthesis of monosubstituted functional derivatives of 1,2-dicarba-closo-dodecaborane (ortho-carborane) is proposed. Reactions of the triethylammonium salt of 1-mercapto-ortho-carborane (Et(3)NH)[1-S-1,2-C(2)B(10)H(11)] with ethyl omega-bromoalkyl carboxylates and omega-bromoalkylnitriles in ethanol result in the corresponding carboranyl esters and nitriles that in turn can be converted to carborane-based carboxylic acids 1-HOOC(CH(2))(n)S-closo-1,2-C(2)B(10)H(11) (n = 1-4). Mild deboronation of the closo-carborane cage with CsF in ethanol gives caesium salts of the corresponding nido-carboranes Cs[7-HOOC(CH(2))(n)S-nido-7,8-C(2)B(9)H(11)]. This approach is suitable for synthesis of compounds to be used in boron neutron capture therapy and radionuclide diagnostics of cancer.
Stogniy
Marina Yu
MY
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991, Moscow, Russia.
Sivaev
Igor B
IB
Petrovskii
Pavel V
PV
Bregadze
Vladimir I
VI
D001880:Boranes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
D001880:Boranes; D013438:Sulfhydryl Compounds