Rhodium-Catalyzed Denitrogenative Diazole–Triazole Coupling toward Aza-Bridged Structures and Imidazole-Based Chelating Ligands

1,4,8-Triazaocta-1,3,5,7-tetraenes, generated in situ by Rh2(Piv)4-catalyzed denitrogenative coupling of pyrazoles with 1-sulfonyl-1,2,3-triazoles, smoothly form 2,6,8-triazabicyclo[3.2.1]­octa-3,6-dienes via intramolecular aza-Diels–Alder cycloaddition. This domino reaction, combined with the subse...

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Bibliographic Details
Published in:Organic letters 2021-06, Vol.23 (11), p.4173-4178
Main Authors: Strelnikova, Julia O, Koronatov, Alexander N, Rostovskii, Nikolai V, Khlebnikov, Alexander F, Khoroshilova, Olesya V, Kryukova, Mariya A, Novikov, Mikhail S
Format: Article
Language:English
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Summary:1,4,8-Triazaocta-1,3,5,7-tetraenes, generated in situ by Rh2(Piv)4-catalyzed denitrogenative coupling of pyrazoles with 1-sulfonyl-1,2,3-triazoles, smoothly form 2,6,8-triazabicyclo[3.2.1]­octa-3,6-dienes via intramolecular aza-Diels–Alder cycloaddition. This domino reaction, combined with the subsequent thermal or acid-catalyzed rearrangement of the cycloadducts, provides direct and flexible access to N-sulfonylated (Z)-2-(2-aminovinyl)­imidazoles.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01092