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Journal of the Brazilian Chemical Society

Print version ISSN 0103-5053On-line version ISSN 1678-4790

Abstract

ROSA, Flávia A. F. da; REBELO, Ricardo A.  and  NASCIMENTO, Maria G.. Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA. J. Braz. Chem. Soc. [online]. 2003, vol.14, n.1, pp.11-15. ISSN 0103-5053.  http://dx.doi.org/10.1590/S0103-50532003000100003.

The synthesis of 5,6-methylenedioxy-indol-3-yl-methanoic acid 8 and 5,6-methylenedioxy-indol-3-yl-acetic acid 13 is described. Piperonal was employed as starting material, and the construction of the heterocyclic ring based on the Hemetsberger reaction of the corresponding b-azidostyrene was highly regiospecific. Compound 8 was obtained as a key intermediate towards 13, and a Mannich reaction was used to introduce the required alkyl side chain. The route comprised eight steps giving 13 in 26% overall yield. The formation of the indolic ring via reductive cyclisation of o,b-dinitrostyrene is also presented.

Keywords : indolecarboxylic acids; nitrene insertion; piperonal; plant growth regulator.

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