Advances in the Synthesis of Heterocycles with Two and Three Heteroatoms using Hydrazonoyl Halides

Helvetica Chimica Acta, Journal Year: 2024, Volume and Issue: 107(7)

Published: April 30, 2024

Abstract The review covers the results of studies published in literature on use hydrazonoyl halides synthesis five‐ (pyrazoles, thiazoles, triazoles, oxa‐ and thiadiazoles), six‐ (oxa‐ thiadiazines, indazoles, pyridazines, pyrazines, tetrazines) or seven‐membered (benzotriazepine) heterocycles. In formation these heterocycles, main intermediate stage reaction is situ generation nitrilimine, which enters into a cycloaddition with substituted acetylenes (including generated benzynes, naphthynes), allenes, activated olefins, anthranilic acid derivatives, organosulfur compounds (mercaptoaldehydes, mercaptocarboxylic acids) fused Examples are given heterocycles by replacing halogen atom from halide molecule nucleophilic group, followed exhaustive intramolecular cyclization target compound. There discussions reactions nitrilimine to synthesized Knoevenagel condensation product (from CH‐acid compounds, such as di‐ monocarbonyl dinitrile malonic acid) occurs, leading spiro‐linked conventional pyrazoles. Some syntheses biologically active representatives shown.

Language: Английский

Organocatalytic multicomponent coupling to access a highly functionalised tetracyclic furoindoline: interrupted Passerini/Joullié–Ugi cascade reaction

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(83), P. 11701 - 11704

Published: Jan. 1, 2022

The interrupted Passerini reaction of 3-(2-isocyanoethyl)-indole catalysed by 3,5,6-trifluoro-2-pyridone is described. diastereoselectively provided a tetracyclic furolindoline, which proved to be good substrate for the Joullié-Ugi reaction; therefore, sequential Passerini/Joullié-Ugi reactions were performed in one-pot rapidly provide versatile and highly functionalised furoindolines from 3-(2-isocyanoethyl)-indole.

Language: Английский

Divergent synthesis of new naphtho-fused 2-aminoindolines and naphthoxindoles based on straightforward construction of phenanthrene

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: unknown

Published: Nov. 1, 2023

An environmentally friendly, highly atom-economical and operationally simple approach toward the synthesis of naphtho-fused 2-aminoindolines naphthoxindoles starting from biaryl aldehydes secondary amines has been developed. This notable methodology integrates consecutive intramolecular Mannich-type cyclization triggered by dearomatization indole with subsequent aromatization via β-elimination then amination or oxidation at C2-position nucleus. The amine-controlled divergent protocol together an easy product isolation process provides a practical route for first time to access 2-substituted indoline.

Language: Английский