Synthesis of Fused sp 3 -Enriched Imidazoles

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...

Full description

Saved in:
Bibliographic Details
Published in:ChemistryOpen (Weinheim) 2024-11, p.e202400272
Main Authors: Lysenko, Viacheslav, Portiankin, Anton, Shvydenko, Tetiana, Shishkina, Svitlana, Nazarenko, Kostiantyn, Kostyuk, Aleksandr
Format: Article
Language:English
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:2191-1363
2191-1363
DOI:10.1002/open.202400272