Synthesis of (Z)-1-phenylseleno-1,4-diorganyl-1-buten-3-ynes: hydroselenation of symmetrical and unsymmetrical 1,4-diorganyl-1,3-butadiynes

Dabdoub, Miguel J.; Baroni, Adriano C. M.; Lenardão, Eder J.; Gianeti, Thiago R.; Hurtado, Gabriela R.

doi:10.1016/s0040-4020(01)00337-4

Cited by 51 publications

(28 citation statements)

References 23 publications

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“…This regioselectivity is similar to that reported for the methods which use organic solvents. 1,[13][14][15][16][17][18][19][20] When the same protocol was applied to phenyl acetylene 1g, (E)-1,2-bis-phenylseleno styrene 5a was obtained in 85% yield after 3 h at 60 °C (Table 1, entry 7). This result is similar to that obtained under solvent-free conditions.…”

Section: Resultsmentioning

confidence: 99%

“…11,12 In this way, various methods are mentioned for the preparation of vinyl chalcogenides and the most common protocols involve the addition of organo chalcogenol, or the respective chalcogenolate anions, to terminal or internal alkynes. [1][2][3][4][5][6][7][8][9][10][13][14][15][16][17][18][19][20] On the other hand, ionic liquids (ILs) are receiving much attention in organic synthesis, both as recyclable solvents and/or catalysts. [21][22][23][24][25][26][27][28][29][30][31][32] Because product isolation or catalyst recycling is very easy in ILs and, in some cases, rate accelerations and/or selectivity improvements are also observed, they are regarded as environmentally friendly green solvents.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

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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“…Retro-Favorski reaction of 22a-c with KOH under reflux in toluene generated the terminal acetylenes 25a-c with 75% to 79% yield [12,[28][29][30]. Ethynyl-1,2,3-trimethoxybenzene 25d was synthesized by the Corey-Fuchs method (Scheme 1) [12,31].…”

Section: Triazole Derivatives Of Neolignansmentioning

confidence: 99%

Antileishmanial Activity and Structure-Activity Relationship of Triazolic Compounds Derived from the Neolignans Grandisin, Veraguensin, and Machilin G

et al. 2016

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Sixteen 1,4-diaryl-1,2,3-triazole compounds 4-19 derived from the tetrahydrofuran neolignans veraguensin 1, grandisin 2, and machilin G 3 were tested against Leishmania (Leishmania) amazonensis intracellular amastigotes. Triazole compounds 4-19 were synthetized via Click Chemistry strategy by 1,3-dipolar cycloaddition between terminal acetylenes and aryl azides containing methoxy and methylenedioxy groups as substituents. Our results suggest that most derivatives were active against intracellular amastigotes, with IC 50 values ranging from 4.4 to 32.7 µM. The index of molecular hydrophobicity (ClogP) ranged from 2.8 to 3.4, reflecting a lipophilicity/hydrosolubility rate suitable for transport across membranes, which may have resulted in the potent antileishmanial activity observed. Regarding structure-activity relationship (SAR), compounds 14 and 19, containing a trimethoxy group, were the most active (IC 50 values of 5.6 and 4.4 µM, respectively), with low cytotoxicity on mammalian cells (SI = 14.1 and 10.6). These compounds induced nitric oxide production by the host macrophage cells, which could be suggested as the mechanism involved in the intracellular killing of parasites. These results would be useful for the planning of new derivatives with higher antileishmanial activities.

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“…13 Furthermore, compared to the use of other hydroxylated solvents, such as ethanol or glycerol, better results have been obtained in the synthesis of vinyl chalcogenides using PEG-400. 12,14,15 In this sense, we describe herein our results on the hydrochalcogenation of 1,4-diorganyl-1,3-butadiynes 1 under mild reaction conditions using diaryl dichalcogenides 2 and PEG-400 as solvent (Scheme 1). The selective product formation 3 or 4 was obtained by a simple temperature Vol.…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400

Lara¹,

Soares²,

Jacob³

et al. 2016

Journal of the Brazilian Chemical Society

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We present here our results on the temperature controlled, selective hydrochalcogenation of 1,4-diorganyl-1,3-butadiynes with nucleophilic species of selenium, tellurium and sulfur generated in situ from the respective diaryl dichalcogenide and NaBH 4 . Using polyethylene glycol (PEG)-400 at 30 o C the (Z)-chalcogenoenynes are obtained and at 90 o C the (Z,Z)-bis-chalcogen-1,3-butadienes are produced in good to excellent yields. Alternatively to conventional oil bath heating, the use of microwave irradiation is also presented as an alternative energy source that provides the expected products in few minutes.

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Synthesis of (Z)-1-phenylseleno-1,4-diorganyl-1-buten-3-ynes: hydroselenation of symmetrical and unsymmetrical 1,4-diorganyl-1,3-butadiynes

Cited by 51 publications

References 23 publications

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

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

Antileishmanial Activity and Structure-Activity Relationship of Triazolic Compounds Derived from the Neolignans Grandisin, Veraguensin, and Machilin G

Selective Synthesis of (Z)-Chalcogenoenynes and (Z,Z)-1,4-bis-Chalcogenbuta-1,3-dienes Using PEG-400

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