BIOMAT Database Logo BIOMAT Database Logo

Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of 5-Sulfonamidoimidazoles. 2018

Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
St. Petersburg State University, Institute of Chemistry , 7/9 Universitetskaya nab. , St. Petersburg 199034 , Russia.

An effective method for the synthesis of fully substituted 5-sulfonamidoimidazoles by Rh(II)-catalyzed transannulation of 1,2,4-oxadiazole derivatives with N-sulfonyl-1,2,3-triazoles is reported. The reaction works well with both aromatic 1,2,4-oxadiazoles and 1,2,4-oxadiazol-5-ones providing a flexible approach to N-(alkoxy/amino)carbonyl- and N-alkyl-substituted imidazoles. Both the disclosed reactions are completely regioselective and provide the first examples of a carbenoid-mediated transformation of N,N,O-heterocycles.

UI MeSH Term Description Entries

Related Publications

Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles.
October 2016, Organic letters,
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Rh(II)-Catalyzed Highly Diastereoselective Cascade Transannulation of N-Sulfonyl-1,2,3-triazoles and Vinyl Benzoxazinanones.
May 2019, Organic letters,
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.
March 2013, Journal of the American Chemical Society,
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Cascade Rh(ii) and Yb(iii) catalyzed synthesis of substituted naphthofurans via transannulation of N-sulfonyl-1,2,3-triazoles with β-naphthols.
April 2019, Chemical communications (Cambridge, England),
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Synthesis of 6-Substituted Piperidin-3-ones via Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles with Electron-Rich Aromatic Nucleophiles.
June 2017, Organic letters,
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles and epoxides: regioselective synthesis of substituted 3,4-dihydro-2H-1,4-oxazines.
September 2014, Organic letters,
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Rh-catalyzed transannulation of N-tosyl-1,2,3-triazoles with terminal alkynes.
July 2011, Organic letters,
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Dirhodium-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles to 2,3-Dehydropiperazines.
August 2023, The Journal of organic chemistry,
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Rhodium Catalyzed Synthesis of Benzopyrans via Transannulation of N-Sulfonyl-1,2,3-triazoles with 2-Hydroxybenzyl Alcohols.
July 2018, Organic letters,
Julia O Strelnikova, and Nikolai V Rostovskii, and Galina L Starova, and Alexander F Khlebnikov, and Mikhail S Novikov
Rh(II)-Catalyzed Denitrogenative Reaction of N-Sulfonyl-1,2,3-triazoles with Quinolones and Isoquinolones.
October 2023, Chemistry, an Asian journal,
Copied contents to your clipboard!