Phosphane‐Catalyzed Knoevenagel Condensation: A Facile Synthesis of α‐Cyanoacrylates and α‐Cyanoacrylonitriles

Yadav, J. S.; Reddy, B. V. Subba; Basak, A. K.; Visali, B.; Narsaiah, A. Venkat; Nagaiah, K.

doi:10.1002/ejoc.200300513

Cited by 164 publications

(47 citation statements)

References 32 publications

(5 reference statements)

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“…This improved method gave a higher yield (95%) than reported before (85%, [11]), and the compound was obtained in analytically pure state without further purification (mp 225 -2268C; reported: 219 -2208C [12], 221 -2238C [13], 228 -2308C [14]). Compound 10b reacted with cyclohexa-1,3-dione 11a and with dimedone 11b (Scheme 2) to afford the chromene derivatives 12a and 12b, respectively, similar to the behavior of 10a towards the same diketones [4].…”

Section: Resultsmentioning

confidence: 88%

Synthesis and Molluscicidal Activity of New Chromene and Pyrano[2,3‐c]pyrazole Derivatives

Abdelrazek

Metz

Kataeva

et al. 2007

Archiv der Pharmazie

228

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The chromene derivative 4 reacts with acetic anhydride, phenylisothiocyanate and ethyl orthoformate to afford the N-acetyl derivative 6, the chromenopyrimidine 8 and the formimidate 9, respectively. 2-(1H-Indol-3-ylmethylene)-malononitrile 10b reacts with 1,3-cyclohexanedione and dimedone 11a, b to afford the 4(3-indolyl)-chromene derivatives 12a, b respectively, and with the pyrazolone derivatives 13a-d to afford the arylidene exchange derivatives 14a-c and the pyranopyrazole derivative 15, respectively. The arylidene derivatives 10a, b react also with indane-1,3-dione 16 to afford the arylidene exchange derivatives 18a, b. The molluscicidal activity of the synthesized compounds towards Biomphalaria alexandrina snails, the intermediate host of Schistosoma mansoni, was investigated and most of them showed weak to moderate activity.

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Section: Resultsmentioning

confidence: 88%

Synthesis and Molluscicidal Activity of New Chromene and Pyrano[2,3‐c]pyrazole Derivatives

Abdelrazek

Metz

Kataeva

et al. 2007

Archiv der Pharmazie

228

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“…The solvent-free reactions are especially appealing as they provide an opportunity to work with open vessels, so it avoids the risk of high-pressure development. In continuation of our research program on developing new synthetic methodologies in solvent-free conditions [19][20][21][22][23][24], herein we wish to report, an efficient, procedure for the alkylation of different malonates with various substituted halonitro benzenes using K 2 CO 3 -neutral alumina (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Microwave Promoted Alkylation of Halonitrobenzene with Malonates in Solvent-free Medium

Akkirala

2007

Catal Lett

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The alkylations on different substituted halonitro benzenes have been demonstrated with various malonates under the influence of microwaves irradiation. The reactions were catalyzed by potassium carbonate and benzyltriethylammoniumchloride. The salient features of this methodology are mild reaction conditions, high regioselectivity, rapid conversions, solvent-free medium and easy isolation of products

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“…Evolution of microwave irradiation 299 a-cyanoacrylates and a-cyanoacrylonitriles 55 [68] in excellent yields with (E)-geometry under microwave irradiation (Scheme 17). Tetra-n-butylammonium hydroxide (TBAH) has been utilized as a novel and efficient catalyst for the Knoevenagel condensation of aldehydes 56 with acidic methylene compounds such as methyl-and ethylcyanoacetate, malononitrile, and cyanoacetamide to afford substituted olefins 57 (Scheme 18) under microwave irradiation [69].…”

Section: Scheme 17mentioning

confidence: 99%

Evolution of microwave irradiation and its application in green chemistry and biosciences

2011

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Microwave-assisted organic reactions have been applied as an effective technique in organic synthesis. Microwave irradiation often leads to shorter reaction times, increased yields, easier workup, matches with green chemistry protocols, and can enhance the region and stereo selectivity of reactions. In fact, the high usefulness of microwave-assisted synthesis encouraged us to increase the efficiency of several organic transformations and synthesis. High-speed microwave-assisted chemistry has attracted a considerable amount of attention in recent years and has been applied successfully in various fields of synthetic organic chemistry, proteins, peptides, drug discovery, and green chemistry. The various roles of microwaveassisted organic chemistry in green and sustainable chemistry are discussed, beginning with the strategies, technologies, and methods that were employed routinely at the time of the first reports of microwave applications. Microwave processing has several advantages over conventional sintering/heating, such as the reduction in cycle time, energy efficiency, eco-friendliness, and providing finer microstructures, leading to improved mechanical properties. Herein, we also describe the evolution of the microwave and some early applications of microwave assistance in the biomolecular sciences and treatment of solid malignant tumors.

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Phosphane‐Catalyzed Knoevenagel Condensation: A Facile Synthesis of α‐Cyanoacrylates and α‐Cyanoacrylonitriles

Cited by 164 publications

References 32 publications

Synthesis and Molluscicidal Activity of New Chromene and Pyrano[2,3‐c]pyrazole Derivatives

Synthesis and Molluscicidal Activity of New Chromene and Pyrano[2,3‐c]pyrazole Derivatives

Microwave Promoted Alkylation of Halonitrobenzene with Malonates in Solvent-free Medium

Evolution of microwave irradiation and its application in green chemistry and biosciences

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