Synthèse des Thiénopyridines

Eloy, F.; Deryckere, A.

doi:10.1002/bscb.19700790505

Cited by 42 publications

(10 citation statements)

References 15 publications

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“…The facility of these cyclization reactions, irrespective of the substitution patterns, was somewhat surprising based on existing precedent. As noted in the introduction (Scheme ), there are prior reports of reactions of simple propargylamines reacting with isothiocyanates giving 2‐aminothiazolidines but these earlier methods either rely on Thorpe‐Ingold type acceleration, much more forcing conditions (e.g., heat or microwave irradiation) or require lengthier reaction times in comparison to our observations where a thiazolidine is obtained under exceptionally mild conditions (r.t. for 2 h) . In contrast, Dethe and coworkers have shown that when various propargylamines and isothiocyanates are reacted in DMF with NaOH as base the corresponding imidazothione (cf.…”

Section: Resultsmentioning

confidence: 99%

“…( E )‐ N ‐Phenyl‐5‐methylidenethiazolidin‐2‐imine (30a): Synthesized following general procedure B, (50 mg, 0.9 mmol), purified by column chromatography (ethyl acetate/hexanes = 1.5:8.5) to afford compound 30a (138 mg, 80 %) as a light‐brown solid. m.p.…”

Section: Methodsmentioning

confidence: 99%

“…Specifically, instead of isolating the thiourea 1 (X = S), we obtained thiazolidines in excellent yields instead. The conversion of propargylamines and isothiocyanates to the thiazolidine or thiazole has been known for a number of years (see Scheme ), however, generally relatively forcing conditions (heating neat, refluxing in toluene or microwave irradiation) were employed. While these reactions are experimentally convenient, depending upon the structures of the precursors, there can be issues with aromatization and formation of other by‐products .…”

Section: Introductionmentioning

confidence: 99%

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Tandem Thioacylation‐Intramolecular Hydrosulfenylation of Propargyl Amines – Rapid Access to 2‐Aminothiazolidines

2019

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An investigation directed towards the preparation of α‐substituted propargyl thioureas from the corresponding propargylamine resulted in a tandem thioacylation/anti‐hydrosulfenylation and the formation of the corresponding thiazolidine in excellent (46–98 %) yields rather than the anticipated thiourea. Initial interpretation of this outcome was formulated in terms of the highly substituted nature of the α‐carbon of these amines resulting in steric acceleration, however, even simple propargylamines engage in this chemistry. In light of these observations, it was determined subsequently that the formation of the thiourea is quite rapid, but cyclization occurred during chromatographic purification and is in fact facilitated by silica gel. Control reactions and monitoring the progress of the reaction by NMR spectroscopy clearly indicate that the cyclization is relatively slow until either purification or the introduction of silica gel results in cyclization. Subsequently, it was found that even the parent system afforded the thiazolidine when the reaction was conducted on silica gel. Overall, the reaction is tolerant of a variety of substitution patterns, internal and terminal alkynes and isothiocyanates providing rapid access to 2‐aminothiazolidines.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Tandem Thioacylation‐Intramolecular Hydrosulfenylation of Propargyl Amines – Rapid Access to 2‐Aminothiazolidines

2019

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“…The ligand thieno[3,2-c]pyridine (thpy) has been prepared by a procedure described elsewhere (ELOY et al, 1970).…”

Section: Methodsmentioning

confidence: 99%

Thieno[3,2-c]Pyridine Complex of Ni(II) with Unusual Magnetic Properties

Miklovič

Baran

Boča

2016

Nova Biotechnologica Et Chimica

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Thieno[3,2-c]pyridine (thpy) has been prepared in a free form and embodied into the [Ni(thpy) 2 (H 2 O) 2 (ac) 2 ] complex as a ligand. The X-ray structure shows a molecular structure of the complex with Ni−O(ac) = 2.059, Ni−OH 2 = 2.078, and Ni−N(thpy) = 2.124 Ǻ. Electronically the complex behaves like a compressed tetragonal bipyramid. The molecular units are linked into a complex system of hydrogen bonds. Two units show a π−π stacking of the aromatic rings (3.8 Ǻ). There are planes of tetragons formed of the nickel atom with the in-plane Ni...Ni separation of 7.74 Ǻ and the inter-plane Ni...Ni contacts at a = 9.65 Ǻ. The effective magnetic moment shows a gradual decrease on cooling from the room temperature and an abrupt drop below 20 K typical for the zero-field splitting of S = 1 systems. Above the room temperature the effective magnetic moment shows anomalies -a decrease and then an increase.

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“…Firstly, the generation of such skeletone was recorded as a result of the intramolecular cyclization of β ‐ketoacid amide, forming only two thieno[2,3‐ g ]indolizine derivatives . Secondly, a general methodology for the preparation of triheterocyclic compounds has been found by the mesoionic cycloaddition of dipolarophiles to oxazolones and Reissert compounds . Thus, thieno[2,3‐ g ]indolizine derivatives containing ester groups in the pyrrole moiety have been synthesized …”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis and Biological Evaluation of New Thieno[2,3‐g]indolizine Derivatives

et al. 2020

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An effective approach to the synthesis of thieno[2,3‐g]indolizine derivatives has been developed. A wide variety of reagents such as unsaturated aldehydes, methylvinylketone, esters of acrylic acid, maleic anhydride, methyl propiolate, dimethyl and diethyl acetylenedicarboxylates in the construction of functionally diverse rarely encountered tricyclic system has been used. A high number of structurally various thieno[2,3‐g]indolizines has been obtained in domino reactions with medium and high yields, the influence of solvents on the course of transformations has been studied, and the presence of moderate cytotoxic activity for a number of compounds has been established.

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Synthèse des Thiénopyridines

Abstract: Des thiknopyridones isombres ont ktb obtenues par cyclisation d'isocyanates de (jT-thiCnyl)vinyle, puis transformdes en thiknopyridines correspondantes.

Cited by 42 publications

References 15 publications

Tandem Thioacylation‐Intramolecular Hydrosulfenylation of Propargyl Amines – Rapid Access to 2‐Aminothiazolidines

Tandem Thioacylation‐Intramolecular Hydrosulfenylation of Propargyl Amines – Rapid Access to 2‐Aminothiazolidines

Thieno[3,2-c]Pyridine Complex of Ni(II) with Unusual Magnetic Properties

Facile Synthesis and Biological Evaluation of New Thieno[2,3‐g]indolizine Derivatives

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