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 high...
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2003-01-01
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| Series: | Journal of the Brazilian Chemical Society |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000100003 |
| _version_ | 1811261185806303232 |
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| author | Rosa Flávia A. F. da Rebelo Ricardo A. Nascimento Maria G. |
| author_facet | Rosa Flávia A. F. da Rebelo Ricardo A. Nascimento Maria G. |
| author_sort | Rosa Flávia A. F. da |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T18:58:52Z |
| format | Article |
| id | doaj.art-6bab5f4771304d9c8afa68b9c7392046 |
| institution | Directory Open Access Journal |
| issn | 0103-5053 |
| language | English |
| last_indexed | 2024-04-12T18:58:52Z |
| publishDate | 2003-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Journal of the Brazilian Chemical Society |
| spelling | doaj.art-6bab5f4771304d9c8afa68b9c73920462022-12-22T03:20:13ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532003-01-011411115Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAARosa Flávia A. F. daRebelo Ricardo A.Nascimento Maria G.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.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000100003indolecarboxylic acidsnitrene insertionpiperonalplant growth regulator |
| spellingShingle | Rosa Flávia A. F. da Rebelo Ricardo A. Nascimento Maria G. Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA Journal of the Brazilian Chemical Society indolecarboxylic acids nitrene insertion piperonal plant growth regulator |
| title | Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA |
| title_full | Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA |
| title_fullStr | Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA |
| title_full_unstemmed | Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA |
| title_short | Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA |
| title_sort | synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid iaa |
| topic | indolecarboxylic acids nitrene insertion piperonal plant growth regulator |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000100003 |
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