Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA
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 beta-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,beta-dinitrostyrene is also presented.
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| Main Authors: | , , |
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| Format: | Digital revista |
| Language: | English |
| Published: |
Sociedade Brasileira de Química
2003
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| Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000100003 |
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