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

作者信息

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

机构信息

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

出版信息

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

1,4,8-Triazaocta-1,3,5,7-tetraenes, generated in situ by Rh(Piv)-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 -sulfonylated ()-2-(2-aminovinyl)imidazoles.