| Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent. | |
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MedLine Citation:
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PMID: 17036116 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The reaction of 2-phenyl- and 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2-CH3COOH) in benzene leads mainly to the formation of the isonitroso and 3-nitroso indole derivatives, respectively. When reacted with nitrous acid, 1-methyl-2-phenylindole gives also the corresponding azo-bis-indole in good yields. The reaction of indole with nitrogen dioxide leads to 2-(indol-3-yl)-3H-indol-3-one as the main product together with small amounts of 2-(indol-3-yl)-3H-indol-3-oxime; whereas the major product obtained when the same indole is reacted with nitrous acid is represented by 2-(indol-3-yl)-3H-indol-3-oxime. The reaction of 3-alkyl substituted indoles with nitrogen dioxide is rather complex and results in the formation of different nitro indoles, whereas nitrosation is observed when nitrous acid is used. Crystal structures of 2-(indol-3-yl)-3H-indol-3-one and of 4-nitro-N-acetyltryptamine have been determined by X-ray analysis. |
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Authors:
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Paola Astolfi; Maria Panagiotaki; Corrado Rizzoli; Lucedio Greci |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2006-07-26 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 4 ISSN: 1477-0520 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2006 Sep |
Date Detail:
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Created Date: 2006-10-12 Completed Date: 2007-09-28 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 3282-90 Citation Subset: IM |
Affiliation:
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Dipartimento di Scienze dei Materiali e della Terra, Università Politecnica delle Marche, via Brecce Bianche, I-60131, Ancona, Italy. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Magnetic Resonance Spectroscopy Models, Molecular Molecular Conformation Nitrogen Dioxide* Nitroso Compounds / chemical synthesis*, chemistry* Nitrous Acid* Probability Solvents* Spectrophotometry |
| Chemical | |
Reg. No./Substance:
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0/Nitroso Compounds; 0/Solvents; 10102-44-0/Nitrogen Dioxide; 7782-77-6/Nitrous Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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