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Bioscience, Biotechnology, and Biochemistry Volume 64, 2000 - Issue 4
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Original Articles

Synthesis and Biological Activities of 4-Chloroindole-3-acetic Acid and Its Esters

Masato KATAYAMALaboratory of Bioorganic Chemistry, Department of Chemistry, National Industrial Research Institute of Nagoya
Pages 808-815 | Received 18 Nov 1999, Accepted 15 Dec 1999, Published online: 22 May 2014

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  • 2) Marumo, S., Abe, H., Hattori, H., and Munakata, K., Isolation of a novel auxin, methyl 4-chloroindoleacetate from immature seeds of Pisum sativum. Agric. Biol. Chem., 32, 117-118 (1968).
  • 3) Marumo, S., Hattori, H., Abe, H., and Munakata, K., Isolation of 4-chloroindolyl-3-acetic acid from immature seeds of Pisum sativum. Nature, 214, 959-960 (1968).
  • 4) Reinecke, D. M., 4-Chloroindole-3-acetic acid and plant growth. Plant Growth Regulation, 27, 3-13 (1999).
  • 5) Ernstsen, A. and Sandberg, G., Identification of 4-chloroindole-3-acetic acid and indole-3-aldehyde in seeds of Pinus sylvestris. Physiol. Plant., 68, 511-518 (1986).
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  • 8) Katayama, M. and Futatsuya, F., Synthesis and biological activities of chlorinated indole auxins and antiauxins. Plant Cell Technology (in Japanese), 2, 487-502 (1990).
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  • 10) Somei, M., Kizu, K., Kunimoto, M., and Yamada, F., The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halogeno group and a carbon functional group at the 4-position. Chem. Pharm. Bull., 33, 3696-3708 (1985).
  • 11) Iwao, M. and Motoi, O., Methodology for the efficient synthesis of 3,4-differentially substituted indoles. Fluoride ion-induced elimination-addition reaction of 1-triisopropylsilylgramine methiodides. Tetrahedron Lett., 36, 5929-5932 (1995).
  • 12) Batcho, A. D. and Leimgruber, W., Indoles from 2-methylnitrobenzenes by condensation with formamide acetals followed by reduction: 4-Benzyloxyindole. Org. Syn., 63, 214-225 (1985).
  • 13) Hatano, T., Katayama, M., and Marumo, S., 5,6-Dichloroindole-3-acetic acid as a potent auxin: its synthesis and biological activity. Experientia, 43, 1237-1239 (1987).

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