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Updated: Sep 16, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
4-Oxo-7-Halosubstituted Phenanthroline Diamides Bifunctional Reactivity: A Synthetic Pathway to Unsymmetrical
Roman V Zonov1, Nane A Avagyan1, Pavel S Lemport1
1Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1 Bld. 3, 119991 Moscow, Russia.
Abstract:
An efficient approach to unsymmetrical 1,10-phenanthroline-2,9-dicarboxamides based on the bifunctional reactivity of 4-oxo-7-haloderivatives is reported. These substrates exhibit orthogonal reactivity, enabling selective nucleophilic aromatic substitution at the C7 position alongside electrophilic functionalization of the 4-oxo group under mild conditions. Reactions with a broad range of C-, N-, and O-nucleophiles afford 4-oxo-7-functionalized products in high yields, while subsequent transformations of azido- and hydroxy-substituted derivatives further demonstrate the synthetic versatility of this platform. The observed chemoselectivity is reflected in the highly selective O-functionalization of the 4-oxogroup, with alkylation proceeding under mild conditions. The developed strategy provides a general route to structurally diverse unsymmetrical derivatives and highlights the potential of 4-oxo-7-halo-systems as bifunctional building blocks.
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