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

Julia O Strelnikova; Alexander N Koronatov; Nikolai V Rostovskii; Alexander F Khlebnikov; Olesya V Khoroshilova; Mariya A Kryukova; Mikhail S Novikov

doi:10.1021/acs.orglett.1c01092

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

Org Lett. 2021 Jun 4;23(11):4173-4178. doi: 10.1021/acs.orglett.1c01092. Epub 2021 May 17.

Authors

Julia O Strelnikova¹, Alexander N Koronatov¹, Nikolai V Rostovskii¹, Alexander F Khlebnikov¹, Olesya V Khoroshilova¹, Mariya A Kryukova¹, Mikhail S Novikov¹

Affiliation

¹ Institute of Chemistry, St. Petersburg State University, 7/9 Universitetskaya nab., St. Petersburg 199034, Russia.

PMID: 33999636
DOI: 10.1021/acs.orglett.1c01092

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't