Selective 5-exo-dig Cyclization of in Situ Synthesized N-Boc-2-Aminophenyl Ethoxyethynyl Carbenols: Synthesis of Multifunctional Indoles and Their Derivatives
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Thirupathi, Nuligonda
Kumar, Y K Kant, Ruchir Reddy, M S |
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| Date |
2014-08-05T07:05:08Z
2014-08-05T07:05:08Z 2014 |
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| Identifier |
Advanced Synthesis & Catalysis, 2014, 356(8), 1823–1834
http://hdl.handle.net/123456789/1342 |
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| Description |
A method to prepare 3-substituted-2-formyl indole derivatives from N-Boc o-aminoarylketones and ethoxyacetylene through a cascade of reactions in a single operation that included a metal/catalyst free nucleophile triggered 5-exo-dig cyclization and acid mediated 1,3-allyl alcohol isomerization (1,3-AAI) is described. A variety of aryl, vinyl and alkynyl groups are introduced at C3 of indole-2-carboxaldehyde while having a high functional group compatibility. The 3-alkynyl adducts, which are highly valuable substrates for diversity oriented synthesis, are further transformed to useful carboline and carbazole derivatives through novel pathways.
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424439 bytes
application/pdf |
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| Language |
en
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| Relation |
CSIR-CDRI Communication No. 8624
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| Subject |
Alkyne
Cyclization Indole Carboline Carbazole |
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| Title |
Selective 5-exo-dig Cyclization of in Situ Synthesized N-Boc-2-Aminophenyl Ethoxyethynyl Carbenols: Synthesis of Multifunctional Indoles and Their Derivatives
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| Type |
Article
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