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

Дмитрий А. Шубин, Дмитрий Н. Кузнецов, Константин И. Кобраков, Алексей М. Старосотников, Наталья Л. Меркулова
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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


Keywords


(Z)-2-arylidene-4,6-dihydroxy-7-methylbenzofuran-3(2H)-ones; aurones; benzofuran-3(2Н)-one; methylaureusidin; 2-methylphloroglucinol; 2,4,6-trihydroxytoluene

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