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Comparative evaluation of a Pictet-Spengler protocol in microwave-assisted conversions of tryptamine with aryl- and carboxyaryl aldehydes: Role of ring strain in cyclocondensation of the primarily formed carboxyaryl-substituted β-carbolines

Monatshefte fur Chemie, ISSN: 0026-9247, Vol: 144, Issue: 9, Page: 1381-1387
2013
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An efficient microwave-assisted Pictet-Spengler protocol employing boric acid/acetic acid as a catalytic system was elaborated for the synthesis of 1-aryl-β-carbolines. Under the novel conditions tryptamine and 2-formylbenzoic acid furnished a pentacyclic skeleton in a single step, whereas using o-phthalaldehyde as a coupling partner led to the formation of an isoindolone derivative. Three β-carbolines primarily resulted from the reactions involving carboxy-substituted heteroaryl aldehydes and avoided cyclisation to polycondensed skeletons with enhanced ring strain, as was evidenced by density functional theory (DFT) modelling. © 2013 Springer-Verlag Wien.

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