Synthesis of New Indolecarboxylic Acids Related to the Plant Hormone Indoleacetic Acid IAA
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چکیده
A síntese dos ácidos 5,6-metilenodioxi-indol-3-il-metanóico 8 e 5,6-metilenodioxi-indol-3-ilacético 13 é descrita. Piperonal foi empregado como material de partida, sendo a construção do heterociclo altamente regioespecífica e está fundamentada na reação de Hemetsberger do correspondente β-azidoestireno. O composto 8 foi obtido como intermediário pivotal na preparação de 13, tendo-se conduzida a reação de Mannich para a introdução da cadeia lateral alquílica. A rota sintética empregada englobou oito etapas e conduziu a formação de 13 com rendimento total de 26%. A formação do heterociclo indólico via ciclização redutiva de o, β-dinitroestireno é também apresentada.
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تاریخ انتشار 2003