Clean and atom-economic synthesis of alpha-phenylselenoacrylonitriles and alpha-phenylseleno- alpha,beta-unsaturated esters by knoevenagel reaction under solvent-free conditions

Perin, Gelson; Jacob, Raquel G.; Botteselle, Giancarlo V.; Kublik, Emerson L.; Lenardão, Eder J.; Cella, Rodrigo; Santos, Paulo César S.

doi:10.1590/s0103-50532005000500027

Cited by 23 publications

(9 citation statements)

References 17 publications

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“…Perin et al [47] has used aryl selenoalkanoates for the synthesis of highly functionalized vinyl selenides, which in turn can undergo several transformations like [2 + 2] cycloaddition reactions, Diels Alder reactions and serve as Michael acceptors. Clive et al [48] has reported that 3-(phenylseleno)propanoate can be easily converted by anionic reactions into substrates that undergo sequential ring closing metathesis and radical cyclizations affording bicyclic products.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid

Bhalla

Nagpal

Kumar

et al. 2009

Journal of Organometallic Chemistry

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid

Bhalla

Nagpal

Kumar

et al. 2009

Journal of Organometallic Chemistry

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“…12, 2011 microwave irradiation in "dry media" reducing substantially the reaction times and increasing product yields. [24][25][26] Because of the advantages that microwave irradiation has over conventional reflux methods, we present, herein, the Knoevenagel synthesis of 3-arylacrylonitriles by the reaction of 2-(benzo[d]thiazol-2-yl)acetonitrile with different substituted arylaldehydes. The synthesis has been assisted by microwave irradiation and under solventfree conditions.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis under solvent-free conditions of (E)-2-(Benzo[d]thiazol-2-yl)-3-arylacrylonitriles

Trilleras¹,

Velásquez²,

Pacheco³

et al. 2011

J. Braz. Chem. Soc.

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Uma série de (E)-2-(benzo[d]tiazol-2-il)-3-arilacrilonitrilas foi sintetizada pela condensação de Knoevenagel assistida por microondas, na ausência de solvente, partindo do correspondente 2-(benzo[d]tiazo-2-il)acetonitrila e aldeídos aromáticos, contendo tanto grupos doadores de elétrons, como retiradores. Os tempos de reação foram consideravelmente curtos e os produtos, obtidos em rendimentos moderados (50-75%) e boa pureza. A configuração da dupla ligação da acrilonitrila não pôde ser estabelecida por métodos comuns de RMN. No entanto, estudos teóricos sugerem que nesses compostos o isômero E é mais estável do que o Z, o que está de acordo com algumas evidências experimentais.A series of (E)-2-(benzo[d]thiazol-2-yl)-3-arylacrylonitriles was synthesized by microwave assisted Knoevenagel condensation under solvent-free conditions from the corresponding 2-(benzo[d]thiazol-2-yl)acetonitrile and aromatic aldehydes with electrondonating/electronwithdrawing groups. The reaction times were considerably short and the products obtained in moderate yields (50 to 75%) and good purity. The configuration of the acrylonitrile double bond could not be established by regular NMR methods. However, theoretical studies suggest that the E isomer is more stable than Z, which is in good agreement with some experimental evidences.

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“…In despite of the high versatility of vinyl chalcogenides and the green feature of ILs, their use as solvent for hydrochalcogenation reaction of alkynes was scarcely explored. 33 As a continuation of our studies toward the development of new and cleaner methods for the synthesis of organochalcogenides, [33][34][35][36][37][38][39][40] we report herein the full results on the hydrochalcogenation of alkynes using NaBH 4 and [bmim]BF 4 as recyclable solvent for the synthesis of vinyl selenides and tellurides (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

NaBH4/[bmim]BF4: a new reducing system to access vinyl selenides and tellurides

Lenardão

Gonçalves

Mendes

et al. 2010

J. Braz. Chem. Soc.

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Um método simples e geral foi desenvolvido para a síntese de selenetos e teluretos vinílicos a partir de alquinos terminais e dicalcogenetos de diorganoíla usando NaBH 4 e [bmim]BF 4 como solvente reciclável. Este método eficiente permite a formação preferencial de calcogenetos vinílicos de configuração Z na maioria dos exemplos estudados. Também foi observado que na reação envolvendo fenilacetileno, (E)-bis-fenilcalcogenoestirenos foram obtidos com bons rendimentos e alta seletividade. O líquido iônico foi reutilizado três vezes sem perda da eficiência.A general and simple method for the synthesis of vinyl selenides and tellurides starting from terminal alkynes and diorganyl chalcogenides using NaBH 4 and [bmim]BF 4 as a recyclable solvent was developed. This efficient and improved method furnishes the corresponding vinyl chalcogenides preferentially with Z configuration. We also observed that when the same protocol was applied to phenyl acetylene, (E)-bis-phenylchalcogeno styrenes were obtained in good yields and high selectivity. The ionic liquid was reused up three times without lost of efficiency.

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Clean and atom-economic synthesis of alpha-phenylselenoacrylonitriles and alpha-phenylseleno- alpha,beta-unsaturated esters by knoevenagel reaction under solvent-free conditions

Cited by 23 publications

References 17 publications

Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid

Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid

Microwave-assisted synthesis under solvent-free conditions of (E)-2-(Benzo[d]thiazol-2-yl)-3-arylacrylonitriles

NaBH4/[bmim]BF4: a new reducing system to access vinyl selenides and tellurides

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