A direct entry to the 1-methoxyindole skeleton and to the corresponding indoles by a novel rearrangement: general syntheses of substituted 1-methoxyindoles |
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Authors: | N Selvakumar BYadi ReddyAMalar Azhagan Manoj Kumar KheraJMoses Babu Javed Iqbal |
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Institution: | Department of Discovery Chemistry, Discovery Research, Dr. Reddy's Laboratories Ltd., Miyapur, Hyderabad 500 050, India |
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Abstract: | A short and efficient route to 1-methoxyindoles via a novel rearrangement is disclosed. This route involves only three steps from commercially available nitro compounds. The methodology is also generalized with a variety of examples to afford a series of 2-substituted-1-methoxyindoles possessing an electron-withdrawing group at position 3. In addition, a 1-methoxyindole compound 10 was converted to the corresponding indole 11 under mild conditions thereby constituting a new synthesis of substituted indoles. |
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Keywords: | rearrangement alkaloid alkylation decarboxylation nucleophilic catalysis |
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