A Novel and Expeditious Approach to Thiophene-3-carboxylates

Fevig, Thomas L.; Phillips, and W. Gary; Lau, Patrick H. W.

doi:10.1021/jo001376y

Cited by 22 publications

(9 citation statements)

References 15 publications

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“…噻吩环可以通过 Gewald 反应合成 [12～14] , 再利用 Sandmeyer 反应通过 2 位胺基的转化, 进而在二异丙基胺基锂(LDA)的作用下引入硅官能团 [7] , 然而该合成过程收率很低(约 10%). 有文献报道在 LDA 的作用下用硅官能团取代噻吩 2 位氢而直接引入 [15,16] , 然而所涉及反应步骤复杂, 原料难以获得. 也有文献报道了通过改变原料直接引入硅官能团的方法 [17] , 然而原料的获得也需要复杂的合成过程.…”

Section: 结果与讨论unclassified

Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity againstGaeumannomyces graminisvar.tritici.

Xie¹,

Jin²,

Zhao³

et al. 2014

Chin. J. Org. Chem.

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The procedures for synthesizing the substituted ester 2-hydrothiophene-3-carboxylate and its silanization were explored. The reaction conditions were optimized. And with the substituted thiophene as the framework, 20 new thiophene carboxamide derivatives were synthesized. The chemical structures of thiophene carboxamide derivatives were confirmed by 1 H NMR, 13 C NMR, HRMS or elemental analysis techniques. The inhibitory activity against Gaeumannomyces graminis var.tritici was evaluated in vitro by the plate method. The preliminary structure-activity relationship indicated that the substituent bonded to the amide nitrogen atom and the steric hindrance of the substituent at 2nd position of the thiophene carboxamide had a significant influence on the activity. The compounds 7b～7d, 7l, 7m and 7o exhibited very high inhibitory activity. The results would be helpful for the design of lead compounds. 1 结果与讨论

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Section: 结果与讨论unclassified

Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity againstGaeumannomyces graminisvar.tritici.

Xie¹,

Jin²,

Zhao³

et al. 2014

Chin. J. Org. Chem.

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“…Their chemical structures were confirmed by 1 H NMR, 13 C NMR and elemental analysis. The inhibitory activity against Gaeumannomyces graminis var.…”

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confidence: 95%

Synthesis of Thiophene Formyl Thiourea Derivatives and Fungicidal Activity

Cheng¹,

Jin²,

Xie³

et al. 2016

Chin. J. Org. Chem.

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13 New thiophene formyl thiourea derivatives were synthesized via cycloaddition reaction of 3-mercaptobutan-2-one and methyl 3-(substitutedsilyl)propiolate, selective hydrolysis of ester, isothiocyanatation and amination. Their chemical structures were confirmed by 1 H NMR, 13 C NMR and elemental analysis. The inhibitory activity against Gaeumannomyces graminis var. tritici and Rhizoctonia solani was evaluated in vitro by the plate method. The results indicated that most of thiophene formyl thiourea derivatives showed some inhibitory activity against gaeumannomyces graminis var. tritici. Compound 1-cyclopropyl-3-(4,5-dimethylthiophene-3-carbonyl)thiourea (8c) gave the best performance and its inhibitory activity was close to the control level of silthiopham in the concentration of 10 mg/L. The structure analysis showed that the steric hindrance of functional group at the second position of the thiophene formyl thioureas had no obvious effect on the inhibitory activity against gaeumannomyces graminis var. tritici.

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“…If the terminal carboncarbon double bond of acrylic acid can be oxidized, it could be converted to important synthesis intermediates, such as alkyl 3,3-dialkoxypropionates and dimethyl malonate, which are extensively used in organic synthesis. Alkyl 3,3-dialkoxypropionates are used to synthesize a variety of compounds, such as coumains [1], spermine [2], loganin [3], wheat fungicide silthiofams [4,5], and 1-amino-pyrrole-3-carboxylic acid derivatives [6]. Previously, the preparation of alkyl 3,3-dialkoxypropionate was not satisfactory because the high cost of raw materials and low overall yield.…”

Section: Introductionmentioning

confidence: 99%

Acrylic Acid Oxidation to Synthesize Methyl 3,3-dimethoxypropionate

Wang

Zhou

2005

Catal Lett

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Methyl 3,3-dimethoxypropionate was prepared via the oxidation of acrylic acid by oxygen in methanol over PdCl 2 /CuCl 2 catalyst. An acrylic acid conversion of 95.2% with a methyl 3,3-dimethoxypropionate selectivity of 90.6% was obtained at 35°C and 5 atm. The reaction pathway might be that the esterification of acrylic acid in methanol was the first step, then methyl acrylate reacted with oxygen to form an intermediate aldehyde, which could react with methanol to form methyl 3,3-dimethoxypropionate.

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A Novel and Expeditious Approach to Thiophene-3-carboxylates

Cited by 22 publications

References 15 publications

Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity againstGaeumannomyces graminisvar.tritici.

Synthesis of Thiophene Carboxamide Derivatives and Inhibitory Activity againstGaeumannomyces graminisvar.tritici.

Synthesis of Thiophene Formyl Thiourea Derivatives and Fungicidal Activity

Acrylic Acid Oxidation to Synthesize Methyl 3,3-dimethoxypropionate

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