Reactions of indoles with nitrogen monoxide: unexpected formation of azo- bis-indoles from 1,2-disubstituted indoles (original) (raw)
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Tetrahedron Letters, 1999
2-Nitro-l-(phenylsulfonyl)indole (1) undergoes nucleophilic addition reactions with the enolates of diethyl malonate and cyclohexanone, lithium dimethylcuprate, and indole anion to afford the corresponding 3-substituted-2-nitroindoles (4---6, 8, 9) in low to high yields. Reaction of l-(phenylsulfonyl)-2-(trialkylstannyl)indoles 13 and 14 with tetranitromethane affords the novel isoxazolo [5,4-b]indole 15 via a 1,3-dipolar cycioaddition reaction with in situ generated nitro formonitrile oxide (19).
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Chemistry of Heterocyclic Compounds, 1986
Reaction of 3,4-ethylenedioxyphenyldiazonium chloride with ethyl 2-methylacetoacetate and subsequent cyclization of the 3,4-ethylenedioxyphenylhydrazone of ethyl pyruvate gives a 1:4 mixture of 4,5-and 5,6-ethylenedioxy-2-ethoxycarbonylindoles, respectively, from which 4,5-and 5,6-ethylenedioxyindoles are formed by subsequent hydrolysis and decarboxylation.
Chemistry and Biology of indoles and Indazoles: A mini-review
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The present review article is related with the method of preparation, importance and medicinal application of indole and indazoles.The studies of heterocycles is an evergreen field in the branch of organic chemistry and always attract the attention of chemists working not only in the area of natural products but also in the synthetic chemistry. Moreover many useful drugs have emerged from the successful investigation carried out in this branch. The derivatives of indoles and indazoles exhibits antibacterial, anticancer, antionidants, anti-inflammatory, antidiabetic, antiviral, atniproliferative, antituberculosis, antispermetogenic activity, antipsychotic drugs etc.
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ChemInform, 2005
The reaction of 2-iodo-and 2-bromoindoles with silver nitrite in aqueous acetone affords the corresponding 2-nitroindoles in modest to good yields.
Synthesis of Medicinally Important Indole Derivatives: A Review
The Open Medicinal Chemistry Journal, 2021
Indoles constitute a widely occurring functional group in nature and are present in an extensive number of bioactive natural products and medicinally important compounds. As a result, exponential increases in the development of novel methods for the formation of indole core along with site-specific indoles have been established. Conventional methods for the synthesis of indoles are getting replaced with green methods involving ionic liquids, water as a solvent, solid acid catalyst, microwave irradiation and the use of nanoparticles under solvent-free conditions. In addition, there are immense applications of the substituted indoles in diverse fields.