Guanidine-catalyzed Henry reaction and Knoevenagel condensation

Han, Junjie; Xu, Yanchao; Su, Yingpeng; She, Xuegong; Pan, Xinfu

doi:10.1016/j.catcom.2008.04.006

Cited by 69 publications

(24 citation statements)

References 7 publications

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“…19 These results clearly indicate that present catalytic method is superior in terms of reaction time, yield and metal and solvent-free condition at rt.…”

Section: Resultssupporting

confidence: 51%

“…All products are reported in literature. 17,18,19,20 2-Nitro-1-phenylethanol (entry 1) 12, 134.86, 130.24, 129.78, 126.13, 70.20 12, 134.86, 130.24, 129.78, 129.32, 126.13, 124.04, 70.20 (m, 9H), 5.43-5.40 (m, 1H), 4.59-4.48 (m, 2H), 2.49 (bs, 1H). 13 C NMR (CDCl3,50 MHz): 157.86,140.45,130.29,129.83,123.71,12.36,119.11,118.73,115.97,70.50 (m, 1H), 7.91-7.88 (m, 1H), 7.85-7.84 (m, 1H), 7.73-7.71 (m, 1H), 7.26-7.30 (m, 3H), 6.27-6.24 (m, 1H), 4.68-4.65 (m, 2H), 2.89 (bs, 1H).…”

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confidence: 99%

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TMEDA Catalyzed Henry (Nitroaldol) Reaction under Metal and Solvent-free Conditions

2009

Bulletin of the Korean Chemical Society

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The Henry (nitroaldol) reaction proceeds under mild conditions with catalytic amount of tetramethylethylenediamine (TMEDA) to afford β-nitro alkanol in considerably excellent yield. Structurally diverse aldehydes react with nitromethane in presence of 0.3 equiv of TMEDA under solvent-free condition at rt. The low catalytic loading and mild reaction condition are the key features of the catalytic method.

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“…19 These results clearly indicate that present catalytic method is superior in terms of reaction time, yield and metal and solvent-free condition at rt.…”

Section: Resultssupporting

confidence: 51%

mentioning

confidence: 99%

TMEDA Catalyzed Henry (Nitroaldol) Reaction under Metal and Solvent-free Conditions

2009

Bulletin of the Korean Chemical Society

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“…This condensation can be easily conducted in the presence of a variety of catalysts including Lewis acids [140], zeolites [141], amine-functionalized materials [142][143][144], ionic liquids [145,146], and nanomaterials [147,148], each of which gives variable yields of the Knoevenagel adducts. In addition, solid bases [149,150] and organic bases, for example piperidine, pyridine, urea, DABCO, and guanidine [151][152][153], have been used for Knoevenagel condensations.…”

Section: Introductionmentioning

confidence: 99%

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Kiyani

Ghorbani

2014

Res Chem Intermed

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A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the threecomponent tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50°C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in a,b-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyranannulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

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“…1 This aspect has aroused a particular interest in developing new and advantageous synthetic approaches towards this reaction. Different molecular solvents, 2 catalysts (organic bases, 3,4 heterogeneous catalysts, 5 Lewis acids 6 ) and reaction conditions (microwave 7 or ultrasound 8 irradiation) have been applied to ensure sufficiently high yields of the target products. Nevertheless, the utilization of toxic solvents or catalysts and prolonged reaction times are inconsistent with the principles of green and sustainable chemistry 9 and still have to be overcome.…”

Section: Introductionmentioning

confidence: 99%

Designing highly efficient solvents for the Knoevenagel condensation: two novel dicationic dimethyl phosphate ionic liquids

Priede¹,

Briča²,

Udris³

et al. 2015

Arkivoc

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Two novel dicationic dimethyl phosphate ionic liquids have been designed as highly efficient solvents for the Knoevenagel condensation between ethyl cyanoacetate and aldehyde with a decreased reactivity -4-(dimethylamino)benzaldehyde. A simple synthetic strategy has been demonstrated for obtaining the dicationic dimethyl phosphate ionic liquid bearing both aromatic imidazolium and aliphatic ammonium moieties.

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Guanidine-catalyzed Henry reaction and Knoevenagel condensation

Cited by 69 publications

References 7 publications

TMEDA Catalyzed Henry (Nitroaldol) Reaction under Metal and Solvent-free Conditions

TMEDA Catalyzed Henry (Nitroaldol) Reaction under Metal and Solvent-free Conditions

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Designing highly efficient solvents for the Knoevenagel condensation: two novel dicationic dimethyl phosphate ionic liquids

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