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• W3142761234 abstract "The present work describes the use of safrole (36) and its derivative piperonal (35) as starting materials for the synthesis of new 5,6methylenedioxysubstituted indole carboxylic acids structurally related to the indol3-yl acetic acid (IAA, 1). In the preparation of the indole nucleus (50) it was exploited the azide chemistry, where the ester 5,6-methylenedioxy-indol-2-yl-carboxylate (47a) was prepared via nitrene insertion reaction which shown to be highly regiospecific. Alkaline hydrolysis followed by acidic work up gave the 5,6-methylenedioxy-indol2-yl-methanoic acid (48), an analogous of IAA. Finally, the indole nucleus (50) was obtained as an analytically pure compound by means of decarboxylation of (48) in the presence of barium hydroxide under vacuum. The reductive cyclization of the o-β-dinitrostyrene (53) can also be regarded as an efficient methodology in the construction of the indole (50). The target molecule 5,6-methylenedioxy-indol-3-yl-acetic acid (55) was prepared employing classical literature reactions, where should be emphasis the efficient Mannich reaction to the introduction of the alkyl side chain. The route comprised eight steps giving (55) in 26% overall yield. Compounds (47a), (48) and (55) were tested towards their plant growth regulator properties in bioassays specific for auxine activity. The “in vitro” assays were performed in germination chamber whereas the “in vivo” were conducted in green house. The experiments employed seeds of Lactuca sativa and Sorgum bicolor to promote the roots grow, stakes of Malvaviscus arboreus for the induction of rooting stem and Phaseolus vulgaris in the petiole and apical dominance tests. Compound (47a) was submitted only to the root growth test. The observed results from the biological assays were very promising and showed that the 5,6-methylenedioxysubstitutedindole acids, specially the molecule (55), can be regarded as a potential plant growth regulators." @default.
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• W3142761234 date "2003-01-01" @default.
• W3142761234 modified "2023-09-26" @default.
• W3142761234 title "UNIVERSIDADE FEDERAL DE SANTA CATARINA CENTRO DE CIÊNCIAS FÍSICAS E MATEMÁTICAS CURSO DE PÓS-GRADUAÇÃO EM QUÍMICA" @default.
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