SYNTHESIS OF AURONE DERIVATIVES ON THE BASIS OF 2,4,6-TRIHYDROXYTOLUENE

Abstract

2,4,6-Trihydroxytoluene (2-methylphloroglucinol) was used as starting material for the first synthesis of several (Z)-2-arylidene-4,6-dihydroxy-7methylaurones, including a synthetic analog of the natural 7-methylaureusidin, which is currently obtained mainly from the extract of sedge capitata  (Cyperus capitatus). It was shown that the reaction of 2,4,6-trihydroxytoluene with chloroacetonitrile occurred regioselectively, with the formation of 4,6-dihydroxy-7-methylbenzofuran-3(2H)-one, the treatment of which with substituted benzaldehydes gave high yields of the target compounds.

Authors: Dmitry A. Shubin, Dmitry N. Kuznetsov*, Konstantin I. Kobrakov, Alexey M. Starosotnikov, Natal'ya L. Merkulova