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

Authors

  • Дмитрий А. Шубин Russian State University named after A. N. Kosygin (Technology. Design. Art), 1 Malaya Kaluzhskaya St., Moscow 119991
  • Дмитрий Н. Кузнецов Russian State University named after A. N. Kosygin (Technology. Design. Art), 1 Malaya Kaluzhskaya St., Moscow 119991
  • Константин И. Кобраков Russian State University named after A. N. Kosygin (Technology. Design. Art), 1 Malaya Kaluzhskaya St., Moscow 119991
  • Алексей М. Старосотников N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991
  • Наталья Л. Меркулова N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991

DOI:

https://doi.org/10.1007/5221

Keywords:

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

Author Biography

Дмитрий Н. Кузнецов, Russian State University named after A. N. Kosygin (Technology. Design. Art), 1 Malaya Kaluzhskaya St., Moscow 119991

Дмитрий Николаевич Кузнецов

кандидат химических наук, доцент кафедры Органической химии

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Published

2019-12-18

Issue

Vol. 55 No. 12 (2019)

Section

Original Papers