Unconventional stereoselective one-pot synthesis of Knoevenagel-type indoles via in situ condensation of iminium salts with active methylene reagents
| Autor: | Angelo Ranise, Francesco Lucchesini, Andrea Spallarossa, Silvana Alfei, Matteo Caviglia, Chiara Caneva |
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| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
Indole test
Nucleophilic addition Chemistry Active methylene reagents Organic Chemistry One-pot synthesis Iminium E2 anti elimination Biochemistry Combinatorial chemistry chemistry.chemical_compound Drug Discovery Iminium salts Knoevenagel reaction Active methylene reagents Iminium salts Knoevenagel reaction Nucleophilic addition E2 anti elimination Knoevenagel condensation Stereoselectivity Methylene Triethylamine |
| Popis: | A simple one-pot procedure for the stereoselective synthesis of Knoevenagel-type indoles is described. The method is based on the in situ reaction of indole iminium salts (four of them are fully characterized) with acyclic symmetrical and unsymmetrical active methylene reagents in the presence of triethylamine. In general, the overall yields are moderate to good. Some of relevant reaction parameters and steric effects affecting stereoselectivity are discussed. |
| Databáze: | OpenAIRE |
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