Novel, Efficient, and Green Procedure for the Knoevenagel Condensation Catalyzed by Diammonium Hydrogen Phosphate in Water

doi:10.1080/00397910600781471

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Novel, Efficient, and Green Procedure for the Knoevenagel Condensation Catalyzed by Diammonium Hydrogen Phosphate in Water

Journal Article•DOI•

Novel, Efficient, and Green Procedure for the Knoevenagel Condensation Catalyzed by Diammonium Hydrogen Phosphate in Water

Saeed Balalaie¹, Morteza Bararjanian¹, Shohreh Hekmat², Peyman Salehi³•Institutions (3)

K.N.Toosi University of Technology¹, Islamic Azad University North Tehran Branch², Shahid Beheshti University³

27 Oct 2006-Synthetic Communications (Taylor & Francis Group)-Vol. 36, Iss: 17, pp 2549-2557

TL;DR: In this paper, the condensation of various aromatic and hetero-aromatic aldehydes with active methylene compounds like methyl and ethyl cyanoacetate, malononitrile, and Cyanoacetamide was carried out at room temperature in short periods with very simple workup procedure and good to high yields.

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About: This article is published in Synthetic Communications.The article was published on 2006-10-27. It has received 46 citations till now. The article focuses on the topics: Knoevenagel condensation & Malononitrile.

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Journal Article•DOI•

Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media

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Shahrzad Abdolmohammadi¹, Saeed Balalaie²•Institutions (2)

University of Tehran¹, K.N.Toosi University of Technology²

30 Apr 2007-Tetrahedron Letters

TL;DR: Diammonium hydrogen phosphate, (NH 4 ) 2 HPO 4 (DAHP), efficiently catalyzes the one-pot, three-component reaction of an aromatic aldehyde, malononitrile and 4-hydroxycoumarin in aqueous media under mild conditions at room temperature, to afford the corresponding dihydropyrano[ c ]chromenes in high yields as discussed by the authors.

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233 citations

Journal Article•DOI•

Diammonium Hydrogen Phosphate: An Efficient and Versatile Catalyst for the One‐Pot Synthesis of Tetrahydrobenzo[b]pyran Derivatives in Aqueous Media

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Saeed Balalaie¹, Morteza Bararjanian¹, Masoumeh Sheikh‐Ahmadi¹, Shohreh Hekmat², Peyman Salehi³ - Show less +1 more•Institutions (3)

K.N.Toosi University of Technology¹, Islamic Azad University North Tehran Branch², Shahid Beheshti University³

01 Apr 2007-Synthetic Communications

TL;DR: Diammonium hydrogen phosphate was used as a mild, efficient, neutral, and cheap catalyst for the synthesis of various 4H•benzo[b]pyran derivatives via a one-pot, three-component condensation of aromatic aldehydes, active methylene compounds, and dimedone in aqueous media as mentioned in this paper.

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127 citations

Journal Article•DOI•

Diammonium hydrogen phosphate as a versatile and efficient catalyst for the one-pot synthesis of pyrano[2,3-d]pyrimidinone derivatives in aqueous media.

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Saeed Balalaie¹, Shahrzad Abdolmohammadi², Hamid Reza Bijanzadeh, Ali Mohammad Amani¹•Institutions (2)

K.N.Toosi University of Technology¹, University of Tehran²

30 May 2008-Molecular Diversity

TL;DR: Diammonium hydrogen phosphate, (NH4)2HPO4, was used as a catalyst for one-pot, three-component condensation reactions consisting of aromatic aldehydes, malononitrile and barbituric/thiobarbiturIC acid in aqueous ethanol at room temperature.

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Abstract: Diammonium hydrogen phosphate, (NH4)2HPO4, was used as a catalyst for one-pot, three-component condensation reactions consisting of aromatic aldehydes, malononitrile and barbituric/thiobarbituric acid in aqueous ethanol at room temperature. This method has the advantages of a simple operation, mild reaction conditions, high yields, by using a less toxic and low cost chemical as a catalyst.

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89 citations

Cites background from "Novel, Efficient, and Green Procedu..."

...There are a few reports regarding the application of DAHP in the preparation of organic compounds, for example in synthesis of dihydropyrimidinones [16], alkenes [17], 1,8-dioxooctahydroxanthenes [18], tetrahydrobenzo[b]pyrans [19], and 3,4-dihydropyrano[c]chromenes [20]....
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Journal Article•DOI•

Diammonium Hydrogen Phosphate as a Neutral and Efficient Catalyst for Synthesis of 1,8‐Dioxo‐octahydroxanthene Derivatives in Aqueous Media

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Fatemeh Darviche¹, Saeed Balalaie¹, Fatemeh Chadegani¹, Peyman Salehi²•Institutions (2)

K.N.Toosi University of Technology¹, Shahid Beheshti University²

01 Apr 2007-Synthetic Communications

TL;DR: In this article, a new and efficient method to synthesize a 3,3,6, 6,9,aryl, 1,8,dioxo-octahydroxanthene derivative using diammonium hydrogen phosphate as catalyst was performed in water at room temperature in a short periods.

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83 citations

Additional excerpts

...4 Xanthene derivatives occupy a prominent position in medicinal chemistry 5 ; they have also been used as dyes, 6 pH‐sensitive fluorescent materials, 7 and laser technology....
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Journal Article•DOI•

Fly ash supported calcium oxide as recyclable solid base catalyst for Knoevenagel condensation reaction

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Deepti Jain¹, Chitralekha Khatri¹, Ashu Rani¹•Institutions (1)

University of Kota¹

01 Sep 2010-Fuel Processing Technology

TL;DR: A new type of solid base catalyst has been prepared by loading of CaO on thermally activated fly ash, with the aim of being used as heterogeneous catalyst for fine chemical production as mentioned in this paper.

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78 citations

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References

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Journal Article•DOI•

Stereoselective organic reactions in water.

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Ulf Lindström¹•Institutions (1)

Lund University¹

19 Jun 2002-Chemical Reviews

1,477 citations

Book•

Domino Reactions in Organic Synthesis

[...]

Lutz F. Tietze¹•Institutions (1)

University of Göttingen¹

11 Sep 2006

TL;DR: It is shown that domino reactions initiated by oxidation or reduction or reduction, as well as other mechanisms, can be inhibited by various materials, such as Na6(CO3)(SO4), Na2SO4, Na2CO3, and so on.

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Abstract: Introduction Cationic domino reactions Anionic domino reactions Radical domino reactions Pericyclic domino reactions Photochemically induced domino processes Transition metal catalysis Domino reactions initiated by oxidation or reduction Enzymes in domino reactions Multicomponent reactions Special techniques in domino reactions

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1,337 citations

"Novel, Efficient, and Green Procedu..." refers background in this paper

...The versatile Knoevenagel reaction has numerous applications in the elegant synthesis of fine chemicals,([2]) hetero Diels–Alder reaction,([3]) and in synthesis of carbocyclic as well as heterocyclic compounds of biological significance.([4]) The reaction is usually catalyzed by bases such as amines or their ammonium salts, ammonia, and sodium ethoxide in organic solvents....
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Book•

Organic reactions in aqueous media

[...]

Chao-Jun Li, Tak Hang Chan

01 Jan 1997

TL;DR: In this article, the authors present a list of metal-mediated reaction types for industrial applications: transition-metal-catalyzed reactions, nucleophilic additions and substitutions, pericyclic reactions, and Oxidations and reductions.

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Abstract: Pericyclic Reactions. Nucleophilic Additions and Substitutions. Metal-- Mediated Reactions. Transition--Metal--Catalyzed Reactions. Oxidations and Reductions. Industrial Applications. Index.

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850 citations

Book•DOI•

Organic synthesis in water

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Paul A. Grieco

01 Jan 1998

TL;DR: Aqueous transition metal catalyzed carbon-carbon bond pairing reactions in aqueous medium were studied in this paper, where base-catalyzed Aldol-and Michael-type condensations were used.

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Abstract: 1. Diels-Alder reactions in aqueous media. 2. Hetero Diels-Alder reactions. 3. Claisen rearrangements in aqueous solution. 4. Carbonyl additions and organometallic chemistry in water. 5. Aqueous transition-metal catalysis. 6. Oxidations and reductions in water. 7. Base-catalyzed Aldol- and Michael-type condensations in aqueous media. 8. Water-stable rare-earth Lewis-acid catalysis in aqueous and organic solvents. 9. Organometallic chemistry in water. 10. Transition metal catalyzed carbon-carbon bond pairing reactions in water. Index.

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842 citations

Journal Article•DOI•

New solvent-free organic synthesis using focused microwaves

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André Loupy, Alain Petit, Jack Hamelin, Françoise Texier-Boullet, Patrick Jacquault, Daniel Mathé - Show less +2 more

01 Sep 1998-Synthesis

760 citations

"Novel, Efficient, and Green Procedu..." refers background in this paper

...Recently, the solvent-free Knoevenagel condensation on solid support promoted by infrared,([9]) ultrasound,([10]) or microwave irradiation([11]) and also in support-free stoichiometric molten condition([12]) has been a matter of interest....
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