Unexpected ring transformation to pyrrolo 3.2-b pyridine derivatives. Fused azolium salts. 22

Zsuzsanna Riedl, Péter Kövér, Tibor Soós, György Hajós, Orsolya Egyed, László Fábián, András Messmer

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Abstract

2-Arylsulfanyl and 2-benzylsulfanylpyridinium N-arylimides (2) easily prepared from 3-aryltetrazolopyridinium salts (1) with aryl and benzylthiolates, respectively, reacted with various dipolarophiles yielding cycloadducts that underwent transformation to give tetrahydropyrrolo[3,2-b]pyridines (5, 6, and 8) in good yields. A similar rearrangement (formation of 15) was also observed in the case of parent derivatives being unsubstituted in position 2 (12). The abscence of any significant solvent effect, comparison of the sulfur and non-sulfur analogues, as well as the stereoselective nature of the observed ring transformation seem to support a sigmatropic mechanism. Structure elucidation of the products has been carried out by single-crystal X-ray diffraction and H-1 NMR experiments.
Original languageEnglish
Pages (from-to)5652-5659
Number of pages8
JournalJournal of Organic Chemistry
Volume68
Issue number14
DOIs
Publication statusPublished - 2003

Keywords

  • 1
  • ISOQUINOLINIUM N-ARYLIMIDES
  • CYCLOADDITION
  • 3-DIPOLES
  • CYCLOADDUCTS
  • REARRANGEMENT

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