The Behaviour of Vicinal Alkyl Aminothiophenecarboxylates in the Sandmeyer and Schiemann Reactions

Corral, Carlos; Lasso, Ana; Lissaveyzky, Jaime; Alvarez-Ins彗, Alberto S�chz; Valdeolmillos, Ana

doi:10.3987/r-1985-06-1431

Cited by 28 publications

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“…Commercially available methyl 3‐aminothiophene‐2‐carboxylate was diazotized using sodium nitrite and tetrafluoroboric acid to give a 70% yield of the corresponding diazonium salt 1 13. This compound showed excellent stability and can be kept safely at −4 °C for unlimited times.…”

Section: Resultsmentioning

confidence: 99%

“…Commercially available methyl 3‐aminothiophene‐2‐carboxylate ( 4 ), olefins 2 , and potassium organotrifluoroborates 5 were used without purification. 2‐Methoxycarbonylthiophene‐3‐diazonium tetrafluoroborate ( 1 )13 and methyl 3‐aminobenzo[ b ]thiophene‐2‐carboxylate ( 7 )17 were prepared as described in the literature. 2‐Methoxycarbonylbenzo[ b ]thiophene‐3‐diazonium tetrafluoroborate ( 8 ) was prepared by diazotization of 7 with sodium nitrite in the presence of HBF 4 following the method for the synthesis of 1 13…”

Section: Methodsmentioning

confidence: 99%

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The use of polyelectrolyte stabilisers for suspension polymerisation: the effect of pH on particle size distribution

Georgiadou

Brooks

2006

Polymer International

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Ammonium polymethacrylate (APMA) and sodium polymethacrylate (PMA‐Na) were used as suspending agents for the suspension polymerisation of methyl methacrylate (MMA). The effect of pH on particle sizes and the stabilisation mechanism were examined. Increasing the pH caused a decrease in the particle sizes, and the formation of fine particles with diameters smaller than 10 µm. The amount of suspending agent required to stabilise a monomer dispersion and to prevent coalescence during suspension polymerisation decreases with increasing pH. The prevailing stabilisation mechanism that governs the dispersion stability is probably the electrosteric mechanism. Copyright © 2006 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

The use of polyelectrolyte stabilisers for suspension polymerisation: the effect of pH on particle size distribution

Georgiadou

Brooks

2006

Polymer International

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“…Thus, 3-chloro- or 3-bromothiophene-2-carboxylates bearing aryl moieties at the C-5 or C-4 position were appropriate starting substrates to construct TT scaffolds according to our strategy. Compounds 2a–k can be prepared either through direct palladium-catalyzed arylation of methyl 3-chlorothiophene-2-carboxylate [19] or through replacement of the amino group in the corresponding 3-aminothiophene-2-carboxylates with a halogen atom by the Sandmeyer reaction [20–21]. The former transformation is preferable for large-scale syntheses, but we failed to repeat the reported procedures.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction

Demina¹,

Kazin²,

Rasputin³

et al. 2019

Beilstein J. Org. Chem.

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Fiesselmann thiophene synthesis was applied for the convenient construction of thieno[3,2-b]thiophene derivatives. Thus, new 5- or 6-aryl-3-hydroxythieno[3,2-b]thiophene-2-carboxylates were obtained by condensation of 5- or 4-aryl-3-chlorothiophene-2-carboxylates, respectively, with methyl thioglycolate in the presence of potassium tert-butoxide. The saponification of the resulting esters, with decarboxylation of the intermediating acids, gave the corresponding thieno[3,2-b]thiophen-3(2H)-ones. The latter ketones were used to synthesize new N,S-heterotetracenes, namely 9H-thieno[2',3':4,5]thieno[3,2-b]indoles by their treatment with arylhydrazines in accordance with the Fischer indolization reaction.

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“…One potential practical application of acetamides 5 was realized in the synthesis of the azo-dye building-block 7. It is well-known that related 3-alkoxycarbonyl and 3-cyanothiophenyl-2-amines containing an unsubstituted 5 position in the thiophene ring are labile compounds which undergo unwanted dimerization upon attempted diazotization [6]. However, this problem can be circumvented by 'blocking' this activated 5-position with a nitro group [7].…”

Section: Resultsmentioning

confidence: 99%

First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction

Eller

Hölzer

2006

Molecules

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Novel 3-acetyl-2-aminothiophenes were prepared from cyanoacetone and 1,4-dithianyl-2,5-diols using a modified Gewald reaction. The syntheses of the corresponding acetamides, as well as that of 3-acetyl-2-amino-5-nitrothiophene -an interesting building-block for thiophene azo dyes -are reported. Detailed spectroscopic investigations ( 1 H-NMR, 13 C-NMR, MS, IR) of the obtained compounds are presented.

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The Behaviour of Vicinal Alkyl Aminothiophenecarboxylates in the Sandmeyer and Schiemann Reactions

Cited by 28 publications

References 0 publications

The use of polyelectrolyte stabilisers for suspension polymerisation: the effect of pH on particle size distribution

The use of polyelectrolyte stabilisers for suspension polymerisation: the effect of pH on particle size distribution

Synthesis of aryl-substituted thieno[3,2-b]thiophene derivatives and their use for N,S-heterotetracene construction

First Synthesis of 3-Acetyl-2-aminothiophenes Using the Gewald Reaction

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