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  • Synthesis and physiological activity of thiophenes and furans with 3- and 4-methoxyacetophenone derivatives.

Synthesis and physiological activity of thiophenes and furans with 3- and 4-methoxyacetophenone derivatives.

Journal of oleo science (2008-01-17)
Shinya Tachibana, Takashi Gotou, Masato Nomura
ABSTRACT

The synthesis and physiological activity of thiophenes and furans with methoxyacetophenone derivatives were examined. 3-Methoxyacetophenone (1) and 4-methoxyacetophenone (2) were converted, respectively, to the oximes (3) and (4) by oximation with hydroxylamine hydrochloride, and to the primary amines (5) and (6) by reduction with LiAlH(4). The primary amine derivatives were further converted into the thiophene and furan compounds (5a) approximately (5h) and (6a) approximately (6h), respectively. Bioassay of these compounds (5a) approximately (5h) and (6a) approximately (6h) on the germination of lettuce(Lactuca satiba) seeds showed that compound (5b) exhibits growthpromoting activity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Lithium aluminum hydride solution, 2.3 M in 2-methyltetrahydrofuran
Sigma-Aldrich
Lithium aluminum hydride solution, 2.0 M in THF
Sigma-Aldrich
Acetanisole, ≥98%, FCC, FG
Sigma-Aldrich
Lithium aluminum hydride solution, 0.5 M in 2-methoxyethyl ether
Sigma-Aldrich
Lithium aluminum hydride solution, 1.0 M in THF
Sigma-Aldrich
Lithium aluminum hydride solution, 1.0 M in diethyl ether
Sigma-Aldrich
Lithium aluminum hydride, hydrogen-storage grade
Sigma-Aldrich
Lithium aluminum hydride, powder, reagent grade, 95%
Sigma-Aldrich
Lithium aluminum hydride, ≥97.0% (gas-volumetric)
Sigma-Aldrich
Lithium aluminum hydride, ≥97.0% (gas-volumetric), tablet (5 g each)
Sigma-Aldrich
Lithium aluminum hydride, pellets, reagent grade, 95%
Sigma-Aldrich
4′-Methoxyacetophenone, 99%