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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Tricotet, Thomas O'shea, Donal F. |
| Description | Author Affiliation: Tricotet T ( Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland.) |
| Abstract | An automated sequential approach for the generation and reactions of 3-hydroxymethylindoles in continuous-flow microreactors is described. Consecutive halogen–magnesium exchanges of four 3-iodoindoles followed by addition to three aldehydes provided twelve 3-hydroxymethylindoles in a multi-microreactor setup. The synthetic flow strategy could be coupled with an in line continuous liquid–liquid extraction workup protocol for each reaction. Further elaboration of each of these indoles within the fluidic setup was achieved by acid-catalysed nucleophilic substitutions with allyltrimethylsilane and methanol used as nucleophiles. Overall, a set of four 3-iodoindoles was converted into thirty-six indole derivatives by a range of transformations including iodo–magnesium exchange/electrophile trapping and acid-catalysed nucleophilic substitution in a fully automated sequential fashion. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 22 |
| Volume Number | 16 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2010-06-11 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Aldehydes Chemistry Halogens Indoles Magnesium Catalysis Molecular Structure Physical Phenomena Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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