Regioselective 2‐Imino‐1,3‐thiazolidine vs. 2‐Imino‐1,3‐oxazolidine Formation from the Vicinal <i>sec</i>‐Amino Alcohol of Desosamine

Ištuk, Zorica Marušić; Vujasinovi, Ines; Čikoš, Ana; Kragol, Goran

doi:10.1002/ejoc.201300266

Cited by 6 publications

(3 citation statements)

References 15 publications

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“…In this context, N -alkyl-2-halopyridinium salts have been used as promoters for the synthesis of different compounds , such as esters, − ketenes, , lactones, , lactams, − peptides, amides, carbodiimides, thiocyanates, pyrazole derivatives, and different polymeric materials …”

Section: Introductionmentioning

confidence: 99%

CS₂/CO₂Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study

et al. 2022

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We report on the reaction of ethylene-terminated heteroatoms (C 2 X; X = N, O, and S) with CS 2 /CO 2 using Mukaiyama reagent (2-chloro-1-methylpyridinium iodide, CMPI) as a promoter for the preparation of imidazolidin-2-one, oxazolidin-2-one, 1,3-dioxolan-2-one, 1,3-dithiolan-2-one, and their thione counterparts at ambient temperature and pressure. Spectroscopic measurements, viz. , 1 H/ 13 C nuclear magnetic resonance (NMR) and ex situ attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy methods verified the reaction of CS 2 /CO 2 with the ethylene-based substrates and subsequently the formation of cyclic products. The experimental data indicated the formation of the enol -form of imidazolidin-2-one and oxazolidin-2-one, while the keto -form was obtained for their thione correspondents. Furthermore, density functional theory calculations revealed the stability of the keto - over the enol -form for all reactions and pointed out the solvent effect in stabilizing the latter.

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Section: Introductionmentioning

confidence: 99%

CS₂/CO₂Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study

et al. 2022

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“…Recently, Sá et al developed a base-mediated [3 + 2] annulation protocol for the synthesis of 2-imino-1,3-thiazolidines through a domino reaction using substituted thioureas and allylic bromides . Kragol and co-workers reported one-pot Mukaiyama regent-induced cyclization of vicinal sec -amino alcohols of desosamine origin for the preparation of regioselective 2-imino-1,3-thiazolidine . In the case of 2-imino-1,3-thiazolines, most of the methods are based on multicomponent reaction of alkynes or α-haloketones or in-situ-generated α-haloketones from ketones with isothiocyanates or ureas …”

Section: Introductionmentioning

confidence: 99%

One-Pot Three-Component Synthesis of 2-Imino-1,3-Thiazolines on Soluble Ionic Liquid Support

2016

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An efficient one-pot, three-component synthesis of 2-imino-1,3-thiazolidines and 2-imino-1,3-thiazolines using ionic liquid-tethered 2-aminobenzimidazoles was reported. The protocol includes reaction of ionic liquid attached 2-aminobenzimidazoles with isothiocyanates to afford isothioureas, followed by its base induced inter and intramolecular nucleophilic displacement reactions with 1,2-dichloroethane (EDC) which results in thiazolidine ring formation. In the next to the last step, the ionic liquid support was removed by methanolysis to deliver 2-imino-1,3-thiazolidines, which were sequentially oxidized with manganese(III) triacetate to yield 2-imino-1,3-thiazolines. The salient feature of this method is the use of 1,2-dichloroethane as a synthetic equivalent for α-haloketone to avoid the use of toxic halogenating reagents.

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“…Drawing from these newly discovered interactions, however, one should be cautious. Having experience with macrocyclic conformational analyses, − we prefer DMSO- d 6 as a solvent because it stabilizes the exchangeable protons through intramolecular hydrogen bonding making their interactions visible. Unfortunately, due to the branimycin molecular size and viscosity of DMSO- d 6 at 25 °C the NOE intensities are close to zero at Larmor frequency of 600 MHz .…”

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confidence: 96%

Reinvestigation of the Branimycin Stereochemistry at Position 17-C

et al. 2016

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A conformational study of branimycin was performed using single-crystal X-ray crystallography to characterize the solid-state form, while a combination of NMR spectroscopy and molecular modeling was employed to gain information about the solution structure. Comparison of the crystal structure with its solution counterpart showed no significant differences in conformation, confirming the relative rigidity of the tricyclic system. However, these experiments revealed that the formerly proposed stereochemistry of branimycin at 17-C should be revised.

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Regioselective 2‐Imino‐1,3‐thiazolidine vs. 2‐Imino‐1,3‐oxazolidine Formation from the Vicinal sec‐Amino Alcohol of Desosamine

Cited by 6 publications

References 15 publications

CS₂/CO₂Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study

CS₂/CO₂Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study

One-Pot Three-Component Synthesis of 2-Imino-1,3-Thiazolines on Soluble Ionic Liquid Support

Reinvestigation of the Branimycin Stereochemistry at Position 17-C

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Regioselective 2‐Imino‐1,3‐thiazolidine vs. 2‐Imino‐1,3‐oxazolidine Formation from the Vicinal sec‐Amino Alcohol of Desosamine

Cited by 6 publications

References 15 publications

CS2/CO2Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study

CS2/CO2Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study

One-Pot Three-Component Synthesis of 2-Imino-1,3-Thiazolines on Soluble Ionic Liquid Support

Reinvestigation of the Branimycin Stereochemistry at Position 17-C

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Product

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CS₂/CO₂Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study

CS₂/CO₂Utilization Using Mukaiyama Reagent as a (Thio)carbonylating Promoter: A Proof-of-Concept Study