Cyclizations of phenylethyl-substituted pyridinecarboxaldehydes

Rajasekhar Reddy Naredla, Douglas A. Klumpp

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Several phenylethyl-substituted pyridinecarboxaldehydes were prepared from 2-bromo-3-pyridine-carboxaldehyde and these substances are found to undergo cyclization reactions in acidic media. In the absence of added nucleophile, acid-promoted cyclization and oxidation (MnO2) provide an efficient route to 10,11-dihydro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-ones. Arene nucleophiles may also be added to the acidic mixture to provide good yields of triarylmethane products. Mechanisms are proposed involving dicationic superelectrophilic intermediates.

Original languageEnglish (US)
Pages (from-to)2137-2141
Number of pages5
JournalTetrahedron
Volume69
Issue number9
DOIs
StatePublished - Mar 4 2013
Externally publishedYes

Keywords

  • Cycloheptabenzopyridine
  • Friedel-Crafts
  • Heterocycle
  • Superacid
  • Superelectrophile

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