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

Riedl, Z., Kover, P., Soos, T., Hajos, G., Egyed, O., Fabian, L. and Messmer, A. (2003) Unexpected ring transformation to pyrrolo 3.2-b pyridine derivatives. Fused azolium salts. 22. Journal of Organic Chemistry, 68 (14). pp. 5652-5659. ISSN 0022-3263

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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.

Item Type: Article
Uncontrolled Keywords: 1,isoquinolinium n-arylimides,cycloaddition,3-dipoles,cycloadducts,rearrangement
Faculty \ School: Faculty of Science > School of Pharmacy
Depositing User: Rachel Smith
Date Deposited: 19 May 2011 11:05
Last Modified: 11 Jan 2019 15:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/30981
DOI: 10.1021/jo034231a

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