New facile tandem route to oxo- and thioxo[1,2,4]triazolo[1,5-a]pyridinium salts

Palkó, Roberta, Riedl, Zsuzsanna, Egyed, Orsolya, Fabian, Laszlo and Hajós, György (2006) New facile tandem route to oxo- and thioxo[1,2,4]triazolo[1,5-a]pyridinium salts. The Journal of Organic Chemistry, 71 (20). pp. 7805-7812.

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2-Arylsulfanyl- and benzylsulfanylpyridinium N-arylimides (2), easily available from tetrazolo[1,5-b]pyridinium salts (1), participate in 1,3-dipolar cycloaddition with aryl isothiocyanates and aryl isocyanates to result in formation of fused thioxo- and oxo[1,2,4]triazolium salts (5 and 12), respectively. This transformation is interpreted as a regular 1,3-cycloaddition followed by spontaneous elimination of the aryl- or benzylsulfanyl group. Formation of these triazolium salts can be followed - under appropriate reaction conditions - by ring-opening reactions to afford some new triazolyldienes (6). Recognition of the intermediate participation of the thiolate anion along the pathway 1 ? 5 allowed elaboration of a simple procedure to 5 implying a tandem reaction sequence.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
UEA Research Groups: Faculty of Science > Research Groups > Drug Delivery and Pharmaceutical Materials (former - to 2017)
Faculty of Science > Research Groups > Pharmaceutical Materials and Soft Matter
Depositing User: Rachel Smith
Date Deposited: 15 Mar 2011 14:59
Last Modified: 08 Feb 2023 17:30
DOI: 10.1021/jo061361l

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