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Synthesis of Fused sp(3)-Enriched Imidazoles.

PubMed
Authors: Lysenko V, Portiankin A, Shvydenko T, Shishkina S, Nazarenko K, Kostyuk A

Year

2025

Paper ID

9569

Status

Peer-reviewed

Abstract Read

~2 min

Abstract Words

100

Citations

0

Abstract

A synthetic approach to imidazoles annulated to saturated six-membered cycles featuring S, SO, NH, NCbz was developed. It was achieved by combining the Neber rearrangement and the Marckwald reaction. The Neber rearrangement applied to cyclic ketones allowed us to prepare in hundred gram quantities previously unknown α-amino ketones. Unstable tosyl ketoximes were used without purification immediately after their preparation. α-Amino ketones react with potassium thiocyanate and cyanate in almost a quantitative yield affording highly pure imidazol-2-thiones or imidazol-2-ones. Desulfurization of imidazole-2-thiones using Raney nickel led to the formation of previously unknown 2-unsubstituted fused imidazoles in high yields.

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  • A synthetic approach to imidazoles annulated to saturated six-membered cycles featuring S, SO, NH, NCbz was developed.

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