Transformations of 2-alkylidene-4-oxothiazolidine vinyl bromides initiated by bromophilic attack of neutral and anionic nucleophiles

Baranac‐Stojanović, Marija; Tatar, Jovana; Stojanović, Milovan; Marković, Rade

doi:10.1016/j.tet.2010.06.057

Cited by 11 publications

(3 citation statements)

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“…Similarly to cyclic ketene S , S -acetals, , 229a – c can be brominated under mild reaction conditions to afford the desired bromo ketene N , S -acetals, which adopt either the Z configuration for 234a / c or the E configuration for 234b , consistent with 1 H NMR data for the amino hydrogen (Scheme ). − Bromo ketene N , S -acetals can be further converted under different conditions, for example, through pyridine-assisted bromine transfer , or functionalization based on DMSO-assisted carbon–bromine bond cleavage …”

Section: Synthesis Of 4-oxothiazolidine Derivatives and Rhodacyanine ...mentioning

confidence: 99%

Chemistry of Ketene N,S-Acetals: An Overview

et al. 2016

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Push-pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are of interest not only for their unique electronic properties but also for their importance as versatile building blocks in organic synthesis. In the world of ketene acetals having the push-pull alkene skeleton, ketene N,S-acetal is most likely the biggest family according to the number and types of these compounds. The first ketene N,S-acetal compound was reported in 1956. As a cyclic ketene N,S-acetal compound, nithiazine, the first lead structure of neonicotinoid insecticides, was reported in 1978. The characteristics of ketene N,S-acetals, which have the structural feature of ketene S,S-acetals and enaminones, make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products. There has been an increasing wealth of information about the synthesis and synthetic applications of ketene N,S-acetals, especially, in recent years. This review provides comprehensive knowledge on the chemistry of ketene N,S-acetals.

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Section: Synthesis Of 4-oxothiazolidine Derivatives and Rhodacyanine ...mentioning

confidence: 99%

Chemistry of Ketene N,S-Acetals: An Overview

et al. 2016

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“…The thioamide and acetylenic acid derivative interactions were studied in different solvents (AcOH, CHCl 3 , MeOH, xylene, and benzene) and at different temperatures (from room temperature to a refluxing temperature). − ,− We performed a series of preliminary experiments for the reaction of 2-cyano-5-phenylpenta-2,4-dienethioamide 3a with DMAD 5a in acetic acid, chloroform, and methanol, both at room temperature and by heating (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…A specific and significant group of thioamide transformations consists of reactions with acetylenedicarboxylic and propiolic acids and their esters. − ,− These reactions are rather complicated due to the diversity of alternative directions caused by the multifunctionality of the reagents involved. Additional functionalities in the thioamide structure increase the number of active centers and expand their synthetic potential to obtain a variety of monoheterocyclic compounds, ensembles, and fused systems.…”

Section: Introductionmentioning

confidence: 99%

Two Approaches for the Synthesis of Fused Dihydropyridines via a 1,6-Electrocyclic Reaction: Fluorescent Properties and Prospects for Application

et al. 2020

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Reactions of penta-2,4-dienethioamides with acetylenedicarboxylic acid, methyl and ethyl esters, and methyl propiolate were systematically studied, and a number of new 2,3-dihydro-5H-thiazolo[3,2-a]pyridines (DTPs) and 4H,6H-pyrido[2,1-b][1,3]thiazines (PTZs) were prepared. A possible mechanism for a multistep domino transformation is suggested, and the key step is the 1,6-electrocyclic reaction. An additional alternative method for the synthesis of new heterocyclic systems was achieved. Evidence of the electrocyclic mechanism of a key step was collected from the analysis of the spatial structure of the synthesized bicyclic nonaromatic pyridines by X-ray diffraction and quantum chemical calculations, as well as from the thermodynamic quantities. DTPs exhibited yellow fluorescence in solution and yellow to red emissions in the solid state. Biological investigations demonstrated the ability of DTPs to penetrate living and fixed cells and presumably accumulate in lysosomes.

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