Syntheses and reactions of 2‐halo‐5‐thiazolecarboxylates

Lee, Len F.; SCHLEPPNIK, F. M.; Howe, Robert K.

doi:10.1002/jhet.5570220631

Cited by 40 publications

(13 citation statements)

References 21 publications

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“…The thiazole nucleus plays a vital role in many biological activities making it one of the extensively studied heterocycles [1][2][3][4][5][6][7][8][9]. For example 2,4-dimethylthiazole-5-carboxamide and 2-methyl-4-trifluoromethylthiazole-5-carboxamide derivatives such as metsulfovax [10] and thifluzamide [11] are known as agricultural fungicides where the 4-trifluoromethylthiazole-5-carboxamide derivatives are usually better than the 4-methylthiazole-5-carboxamides [3].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of novel 2-methyl-4-trifluoromethyl-thiazole-5-carboxamide derivatives

Liu

Zhong

2004

Journal of Fluorine Chemistry

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Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of novel 2-methyl-4-trifluoromethyl-thiazole-5-carboxamide derivatives

Liu

Zhong

2004

Journal of Fluorine Chemistry

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“…Its addition to activated double bonds formed heterocyclic compounds, as for example 1,4-thiazines 119 or pyrroles 120 from 3-aminoacrylates 118 [68].…”

Section: Heterocycles From Disulfur Dichloride and Nitrogen Containinmentioning

confidence: 99%

Poly-sulfur-nitrogen heterocycles via sulfur chlorides and nitrogen reagents

Torroba

1999

J. prakt. Chem.

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Nitrogen and sulfur organic aromatic heterocycles are formally derived from aromatic carbon cycles by a heteroatom taking the place of a ring carbon atom or a complete CH=CH group. The presence of heteroatoms results in significant changes in the cyclic molecular structure due to the availability of unshared pairs of electrons and the difference in electronegativity between heteroatoms and carbon. Therefore, nitrogen and sulfur heterocyclic compounds display physicochemical characteristics and reactivity far from the parent aromatic hydrocarbons. On the other hand, the presence of many nitrogen and sulfur atoms in a ring is normally associated with instability and difficulties in the synthesis but, in fact, surprisingly stable heterocycles with unusual properties can be frequently obtained from simple or- Poly-Sulfur-Nitrogen Heterocycles via Sulfur Chlorides and Nitrogen ReagentsTomás Torroba* Burgos/Spain, Departamento de Química, Facultad de Ciencias, Universidad Received October 28th, 1998, respectively January 4th, 1999Keywords: Conducting materials, Nitrogen heterocycles, Phosphorus heterocycles, Selenium, Sulfur heterocycles Abstract: The family of poly-sulfur-nitrogen heterocycles includes highly stable aromatic compounds that display physicochemical properties with relevance in the design of new materials, especially those relating to molecular conductors and magnets. The interesting characteristics found in many of these heterocycles have led to the development of modern synthetic methods that are the subject of this review. Heterocycles such as 1,2,3-and 1,2,5-thiadiazoles, 1,2,3-and 1,3,2-dithiazoles, 1,2,3,5-dithiadiazoles, thiatriazines, trithiadiganic substrates and the appropriate inorganic reagent. This paper reviews the most common synthetic methods to obtain poly-sulfur-nitrogen heterocyclic systems that lie in the middle way between organic and inorganic chemistry. Carbon atoms confer high stability to such rings, according to the aromaticity and antiaromaticity rules, and the nitrogen-sulfur core gives unusual properties to the compounds, in accordance with their electron rich π-excessive nature. The physicochemical properties of this family of compounds have relevance in the design of new materials, specially concerning organic conductors. In contrast with the number and variety of such heterocycles, the number of synthetic methods to afford them is, in practice, restricted to the availability of the appropriate sulfur reagent. The classification of synthetic methods follows the applications of the most common sulfur reagents to the synthesis of heteroaromatic carbon-nitrogen-sulfur rings and sometimes extends to selenium or phosphorus related heterocycles. Binary inorganic sulfur-nitrogen cycles are covered by some reports from Chivers and Oakley [1]. Some binary S-N rings, as B-F in figure 1, constitute the models and sometimes precursors of the organic members of the series.azines, dithia(and trithia)diazepines, trithiatriazepines, dithia(and trithia)tetrazozines, and fused systems are mo...

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“…4 and phenols were treated with potassium tert-butoxide in THF to yield ethyl 2-(substituted phenoxy)-4-(trifluoromethyl)thiazole-5-carboxylate (5), followed by hydrolysis with sodium hydroxide to form 2-(substituted phenoxy)-4-(trifluoromethyl)thiazole-5-carboxylic acid (6) and then forming the acid chloride (7) by reaction with thionyl chloride. Reaction of the acid chloride 7 with the appropriate amine in the presence of triethylamine results in the desired amide 1.…”

Section: Synthesismentioning

confidence: 99%

“…Ethyl 3-amino-4,4,4-trifluoro-2-butenoate (2) was used as the starting material, which was treated with chloroformylsulfenyl chloride to gave ethyl 2-oxo-4-(trifluoromethyl)-2,3-dihydrothiazole-5-carboxylate (3), followed by chlorination with POCl 3 to provide ethyl 2-chloro-4-(trifluoromethyl)thiazole-5-carboxylate (4) according to the literature procedure [6]. 4 and phenols were treated with potassium tert-butoxide in THF to yield ethyl 2-(substituted phenoxy)-4-(trifluoromethyl)thiazole-5-carboxylate (5), followed by hydrolysis with sodium hydroxide to form 2-(substituted phenoxy)-4-(trifluoromethyl)thiazole-5-carboxylic acid (6) and then forming the acid chloride (7) by reaction with thionyl chloride.…”

Section: Synthesismentioning

confidence: 99%

“…To the reaction mixture was added ethyl 2-chloro-4-(trifluoromethyl)thiazole-5-carboxylate 4[6] (30.0 g, 0.116 mol), stirred at room temperature overnight. After evaporated in vacuum, water was added and extracted with ethyl acetate, washed with 4 M HCl, water and brine, dried over magnesium sulfate, evaporated in vacuum and then purified by silica gel column chromatography to give 39.1 g (88%) of the target compound (5A), as oil.…”

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confidence: 99%

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