FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing a compound of formula (I)
,
where X is selected from S, Se and O; R1 is selected from H, (C1-C6)-alkyl groups, (C6-C22)-aryl groups and (C1-C6)-alkyl(C6-C22)-aryl groups; R2 is selected from H, OH, NR4R5, NHCOR4, OCOR4, where R4 and R5 are identical or different and are selected from H, (C1-C6)-alkyl groups, (C6-C22)-aryl groups, (C1-C6)-alkyl(C6-C22)-aryl groups and protective groups; R3 is selected from OH, CH2OH, COOH, COOR6, where R6 is selected from (C1-C6)-alkyl, CN, CONR4R5, where R4 and R5 have the values given above, and COZ, where Z is a halide; wherein said method involves reaction of a compound of formula (II)
,
where X is selected from S, Se and O; R1' is selected from H, (C1-C6)-alkyl, (C6-C22)-aryl, (C1-C6)-alkyl(C6-C22)-aryl, thiol, thio(C1-C6)-alkyl, thio(C6-C22)-aryl, thio(C1-C6)-alkyl(C6-C22)-aryl, selenol, seleno(C1-C6)-alkyl, seleno(C6-C22)-aryl and selenium (C1-C6)-alkyl(C6-C22)-aryl groups, and R2' is selected from H, (C1-C6)-alkyl groups, (C6-C22)-aryl groups and (C1-C6)-alkyl(C6-C22)-aryl groups; with a compound of formula (III)
,
where R2 and R3 have the values given above for the compound of formula (I), in the presence of at least one agent for initiating a radical addition reaction containing a persulphate and a transition metal in an elemental form or in an oxidised form, where said transition metal is selected from Cu, Zn and Fe, in their elemental form or in an oxidised form, selected from sulphates, phosphates, chlorides, carbonates, hydroxides, nitrites, nitrates, acetates, alcoholates, hydrophosphates and hydrosulphates, as well as their alloys, where said reaction is carried out at a temperature of −20 °C to 40 °C, as well as the use of an agent for initiating a radical addition reaction to obtain compounds of formula (I).
EFFECT: efficient synthesis of compounds by selective radical addition using energy-free and easily industrialized conditions.
9 cl, 5 ex
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