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Catalytic performance of cadmium pyrophosphate in the knoevenagel condensation and one-pot multi-component reaction of chromene derivatives

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Abstract

A simple, efficient, and eco-friendly process for the Knoevenagel condensation between various aromatic aldehydes and active methylene compounds and the synthesis of 2-amino-4H-chromene derivatives via a multi-component reaction of various aromatic aldehydes, malononitrile, and resorcinol catalyzed by mono-ammonium phosphate fertilizer (MAP) modified by cadmium chloride (CdCl2) is described. This synthesis procedure is considered an attractive method due to its excellent yields, short reaction time, green conditions, cost-effectiveness, use of a non-toxic solvent, non-chromatographic purification of products, and recyclability of the catalyst.

Graphical abstract

A simple, efficient, and ecofriendly process is proposed to synthesize 2-amino-4H-chromene and 2-(4-chlorobenzylidene) malononitrile derivatives via the application of cadmium pyrophosphate (Cd2P2O7) as catalyst prepared from the modification of mono-ammonium phosphate fertilizer (MAP) by adding cadmium chloride (CdCl2). The products were obtained with good yields in a short reaction time.

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Reference

  1. Mowry D T 1945 The Knoevenagel Condensation of Aryl Alkyl Ketones with Malononitrile J. Am. Chem. Soc. 67 1050

    Article  Google Scholar 

  2. Garrabou X, Wicky B I M and Hilvert D 2016 Fast Knoevenagel Condensations Catalyzed by an Artificial Schiff-Base-Forming Enzyme J. Am. Chem. Soc. 138 6972

    Article  CAS  PubMed  Google Scholar 

  3. Dhorajiya B D and Dholakiya B Z 2014 Green Chemistry Multicomponent Protocol for Formylation and Knoevenagel Condensation for Synthesis of (Z)-5-Arylaminomethylene Pyrimidine 2, 4, 6-Trione Derivatives in Water Green Chem. Lett. Rev. 7 1

    Article  Google Scholar 

  4. Guiheneuf S, Paquin L, Carreaux F, Durieu E, Roisnel T, Meijer L and Bazureau J P 2014 New 5-Ylidene Rhodanine Derivatives Based on the Dispacamide A Model Mol. Divers. 18 375

    Article  CAS  PubMed  Google Scholar 

  5. Polander L E, Barlow S, Seifried B M and Marder S R 2012 A 2,6-Diformylnaphthalene-1,8:4,5-Bis(Dicarboximide): Synthesis and Knoevenagel Condensation with Malononitrile J. Org. Chem. 77 9426

    Article  CAS  PubMed  Google Scholar 

  6. Kudirka R A, Barfield R M, McFarland J M, Drake P M, Carlson A, Bañas S, et al. 2016 Site-Specific Tandem Knoevenagel Condensation-Michael Addition To Generate Antibody-Drug Conjugates ACS Med. Chem. Lett. 7 994

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Teixeira L H P, Fraga C A M and Barreiro E J 1998 Synthesis of New 1,2-Benzothiazin-3-One Derivatives Designed as Dual Cyclooxygenase-2 and 5-Lipooxygenase Inhibitors J. Braz. Chem. Soc. 9 119

    Article  CAS  Google Scholar 

  8. Watson T J N, Horgan S W, Shah R S, Farr R A, Schnettler R A, Nevill C R, et al. 2000 Chemical Development of MDL 103371: An N -Methyl- d -Aspartate-Type Glycine Receptor Antagonist for the Treatment of Stroke Org. Process Res. Dev. 4 477

    Article  CAS  Google Scholar 

  9. Liang F, Pu Y J, Kurata T, Kido J and Nishide H 2005 Synthesis and Electroluminescent Property of Poly(p-Phenylenevinylene)s Bearing Triarylamine Pendants Polymer 46 3767

    Article  CAS  Google Scholar 

  10. Chanu I H, Devi L R, Khumanthem N, Singh N I, Kumar D and Singh O M 2017 Synthesis of Functionalized Benzo[f]2H-Chromenes and Evaluation of Their Antimicrobial Activities Russ. J. Bioorg. Chem. 43 177

    Article  CAS  Google Scholar 

  11. Conti C, Proietti Monaco L and Desideri N 2014 Synthesis and Anti-Rhinovirus Activity of Novel 3-[2-(Pyridinyl)Vinyl]Substituted-2H-Chromenes and -4H-Chromen-4-Ones Bioorg. Med. Chem. 22 1201

    Article  CAS  PubMed  Google Scholar 

  12. Chung S T, Huang W H, Huang C K, Liu F C, Huang R Y, Wu C C and Lee A R 2016 Synthesis and Anti-Inflammatory Activities of 4H-Chromene and Chromeno[2,3-b]Pyridine Derivatives Res. Chem. Intermed. 42 1195

    Article  CAS  Google Scholar 

  13. Lakshmi B N, Pradeep Rajkumar L A, Arulanandham A, Satheesh Babu N, Gayathri T and Raju A 2012 Anti-Oxidant and Anti-Inflammatory Activity of Synthesized 3(Substituted) Chromen-2-One Int. J. Pharm. Sci. Res. 3 474

    Google Scholar 

  14. Wu J Y C, Fong W F, Zhang J X, Leung C H, Kwong H L, Yang M S, et al. 2003 Reversal of Multidrug Resistance in Cancer Cells by Pyranocoumarins Isolated from Radix Peucedani Eur. J. Pharmacol. 473 9

    Article  CAS  PubMed  Google Scholar 

  15. Chohan Z H, Shaikh A U, Rauf A and Supuran C T 2006 Antibacterial, Antifungal and Cytotoxic Properties of Novel N-Substituted Sulfonamides from 4-Hydroxycoumarin J. Enzyme Inhib. Med. Chem. 21 741

    Article  CAS  PubMed  Google Scholar 

  16. Bonsignore L, Loy G, Secci D and Calignano A 1993 Synthesis and Pharmacological Activity of 2-Oxo-(2H) 1-Benzopyran-3-Carboxamide Derivatives Eur. J. Med. Chem. 28 517

    Article  CAS  Google Scholar 

  17. Zhao H, Neamati N, Hong H, Mazumder A, Wang S, Sunder S, et al. 1997 Coumarin-Based Inhibitors of HIV Integrase J. Med. Chem. 40 242

    Article  CAS  PubMed  Google Scholar 

  18. Akbarian M, Sanchooli E, Oveisi A R and Daliran S 2021 Choline chloride-coated UiO-66-Urea MOF: A novel multifunctional heterogeneous catalyst for efficient one-pot three-component synthesis of 2-amino-4H-chromenes J. Mol. Liq. 325 115228

    Article  CAS  Google Scholar 

  19. Tamilthendral V, Ramesh R and Malecki J G 2022 New ruthenium (ii) catalysts enable the synthesis of 2-amino-4 H-chromenes using primary alcohols via acceptorless dehydrogenative coupling New J. Chem. 46 21568

    Article  CAS  Google Scholar 

  20. Boroumand H, Alinezhad H, Maleki B and Peiman S 2022 Triethylenetetramine-Grafted Magnetic Graphene Oxide (Fe3O4@ GO-NH2) as a Reusable Heterogeneous Catalyst for the One-Pot Synthesis of 2-Amino-4 H-Benzopyran Derivatives Polycycl. Aromat. Compd. 1

  21. Chatterjee R, Bhukta S and Dandela R 2022 Ionic liquid-assisted synthesis of 2-amino-3-cyano-4 H-chromenes: A sustainable overview J. Heterocycl. Chem. 59 633

    Article  CAS  Google Scholar 

  22. Sharma S, Meena M, Sharma H, Yadav D K, Tiwari A and Verma V P 2022 Fe3O4-supported sulfonated graphene oxide as a green and magnetically separable nanocatalyst for synthesis of 2-amino-3-cyano-4 H-chromene derivatives and their in-silico studies Synth. Commun. 52 1926

    Article  CAS  Google Scholar 

  23. Kale S R, Kahandal S S, Burange A S, Gawande M B and Jayaram R V A 2013 Benign Synthesis of 2-Amino-4H-Chromene in Aqueous Medium Using Hydrotalcite (HT) as a Heterogeneous Base Catalyst Catal. Sci. Technol. 3 2050

    Article  CAS  Google Scholar 

  24. Kiyani H and Ghorbani F 2015 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 Res. Chem. Intermed. 41 7847

    Article  CAS  Google Scholar 

  25. Şen B, Lolak N, Paralı Ö, Koca M, Şavk A, Akocak S and Şen F 2017 Bimetallic PdRu/Graphene Oxide Based Catalysts for One-Pot Three-Component Synthesis of 2-Amino-4H-Chromene Derivatives Nano-Struct. Nano-Objects 12 33

    Article  Google Scholar 

  26. Mohammadinezhad A and Akhlaghinia B 2018 Nanofibre Sepiolite Catalyzed Green and Rapid Synthesis of 2-Amino-4H-Chromene Derivatives Aust. J. Chem. 71 32

    Article  CAS  Google Scholar 

  27. Pawar G T, Magar R R and Lande M K 2018 Mesolite: An Efficient Heterogeneous Catalyst for One-Pot Synthesis of 2-Amino-4H-Chromenes Polycycl. Aromat. Comp. 38 75

    Article  CAS  Google Scholar 

  28. Behravesh S, Fareghi-Alamdari R and Badri R 2018 Sulfonated Reduced Graphene Oxide (RGO-SO3H): As an Efficient Nanocatalyst for One-Pot Synthesis of 2-Amino-3-Cyano-7-Hydroxy- 4H -Chromenes Derivatives in Water Polycycl. Aromat. Comp. 38 51

    Article  CAS  Google Scholar 

  29. Mohammadi R, Esmati S, Gholamhosseini-Nazari M and Teimuri-Mofrad R 2019 Novel Ferrocene Substituted Benzimidazolium Based Ionic Liquid Immobilized on Magnetite as an Efficient Nano-Catalyst for the Synthesis of Pyran Derivatives J. Mol. Liq. 275 523

    Article  CAS  Google Scholar 

  30. Moghadasi Z 2019 One-Pot Synthesis of 2-Amino-4H-Chromenes Using L-Proline as a Reusable Catalyst J. Med. Chem. Sci. 2 35

    CAS  Google Scholar 

  31. Chehab S, Merroun Y, Ghailane R, Boukhris S and Souizi A 2022 Na2Ca (HPO4)2, an Efficient, Reusable Eco-Friendly Catalyst for the Synthesis of 1,8-Dioxo-Octahydroxanthenes and Biscoumarin Derivatives Polycycl. Aromat. Comp. 1

  32. Chehab S, Merroun Y, Ghailane T, Ghailane R, Boukhris S, Lakhrissi B and Souizi A 2021 A facile and efficient synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[4, 3-b]pyrans derivatives using phosphate fertilizers MAP, DAP, and TSP as heterogeneous catalysts J. Iran. Chem. Soc. 18 2665

    Article  CAS  Google Scholar 

  33. Merroun Y, Chehab S, Ghailane T, Ghailane R, Boukhris S, Habbadi N, et al. 2020 Comparative study between the Titanium Phosphate TiP2O7 and the Phosphate Fertilizers in the catalysis of the Quinazolin-4(3H)-one derivatives synthesis Mediterr. J. Chem. 10 553

    Article  CAS  Google Scholar 

  34. Hallaoui AE, Chehab S, Ghailane T, Malek B, Zimou O, Boukhriss S, et al. 2020 Application of Phosphate Fertilizer Modified by Zinc as a Reusable Efficient Heterogeneous Catalyst for the Synthesis of Biscoumarins and Dihydropyrano[3,2-c]Chromene-3-Carbonitriles under Green Conditions Polycycl. Aromat. Comp. 41 2083

    Article  Google Scholar 

  35. Merroun Y, Chehab S, Ghailane T, Akhazzane M, Souizi A and Ghailane R 2019 Preparation of tin-modified mono-ammonium phosphate fertilizer and its application as heterogeneous catalyst in the benzimidazoles and benzothiazoles synthesis React. Kinet. Mech. Catal. 126 249

    Article  CAS  Google Scholar 

  36. El Hallaoui A, Chehab S, Malek B, Zimou O, Ghailane T, Boukhris S, et al. 2019 Valorization of the Modified Mono Ammonium Phosphate by Cobalt in the Synthesise of 3,4-Dihydropyrano[c]chromene Derivatives ChemistrySelect 4 3062

    Article  Google Scholar 

  37. Chehab S, Merroun Y, Ghailane T, Ghailane R, Boukhris S and Souizi A 2021 Mono-Ammonium Phosphate Fertilizer Modified by Cadmium: An Efficient and Recyclable Catalyst for 2,3-Dihydroquinazolin-4 (1H)-One Derivatives Synthesis Polycycl. Aromat. Comp. 1

  38. Cao Y, Dai Z, Zhang R and Chen B 2004 A Practical Knoevenagel Condensation Catalyzed by PEG400 and Anhydrous K2CO3 without Solvent Synth. Commun. 34 2965

    Article  CAS  Google Scholar 

  39. Benzekri Z, El Mejdoubi K, Boukhris S, Sallek B, Lakhrissi B and Souizi A 2016 Dicalcium Phosphate Dehydrate DCPD as a Highly Efficient and Reusable Catalyst for Knoevenagel Condensation Synth. Commun. 46 442

    Article  CAS  Google Scholar 

  40. Balalaie S, Bararjanian M, Hekmat S and Salehi P 2006 Novel, Efficient, and Green Procedure for the Knoevenagel Condensation Catalyzed by Diammonium Hydrogen Phosphate in Water Synth. Commun. 36 2549

    Article  CAS  Google Scholar 

  41. Dekamin M G and Eslami M 2014 Highly Efficient Organocatalytic Synthesis of Diverse and Densely Functionalized 2-Amino-3-Cyano-4H-Pyrans under Mechanochemical Ball Milling Green Chem. 16 4914

    Article  CAS  Google Scholar 

  42. Dekamin M G, Eslami M and Maleki A 2013 Potassium Phthalimide-N-Oxyl: A Novel, Efficient, and Simple Organocatalyst for the One-Pot Three-Component Synthesis of Various 2-Amino-4H-Chromene Derivatives in Water Tetrahedron 69 1074

    Article  CAS  Google Scholar 

  43. Rostamizadeh S and Zekri N 2016 An Efficient, One-Pot Synthesis of 2-Amino-4H-Chromenes Catalyzed by (α-Fe2O3)-MCM-41-Supported Dual Acidic Ionic Liquid as a Novel and Recyclable Magnetic Nanocatalyst Res. Chem. Intermediat. 42 2329

    Article  CAS  Google Scholar 

  44. Kai G, Hua-Lan W, Dong F and Zu-Liang L 2008 Basic ionic liquid as catalyst for the rapid and green synthesis of substituted 2-amino-2-chromenes in aqueous media Catal. Commun. 9 650

    Article  Google Scholar 

  45. Nazanin N, Farhad S, Hassan T, Mashhadinezhad M and Mohaddeseh Safarpoor Nikoo L 2018 An affordable DABCO-based ionic liquid efficiency in the synthesis of 3-amino-1-aryl-1H-benzo[f] chromene-2- carbonitrile, 1-(benzothiazolylamino)phenylmethyl-2-naphthol, and 1-(benzoimidazolylamino)phenylmethyl-2-naphthol derivatives J. Iran. Chem. Soc. 15 2147

    Article  Google Scholar 

  46. Bahammou I, Esaady A, Boukhris S, Ghailane R, Habbadi N, Hassikou A and Souizi A 2016 Direct use of mineral fertilizers MAP, DAP, and TSP as heterogeneous catalysts in organic reactions Mediterr. J. Chem. 5 615

    Article  CAS  Google Scholar 

  47. de Resende Filho J B M, Pires G P, de Oliveira F J M G, Teotonio E E S and Vale J A 2017 Knoevenagel Condensation of Aldehydes and Ketones with Malononitrile Catalyzed by Amine Compounds-Tethered Fe3O4@SiO2 Nanoparticles Catal. Lett. 147 167

    Article  Google Scholar 

  48. Hassan H M A, Elshaarawy R F M, Dey S K, Simon I and Janiak C 2017 Microwave-Assisted Hydrothermal Fabrication of Magnetic Amino-Grafted Graphene Oxide Nanocomposite as a Heterogeneous Knoevenagel Catalyst Catal. Lett. 147 1998

    Article  CAS  Google Scholar 

  49. Xu J, Shen K, Xue B and Li Y X 2013 Microporous Carbon Nitride as an Effective Solid Base Catalyst for Knoevenagel Condensation Reactions J. Mol. Catal. Chem. 372 105

    Article  CAS  Google Scholar 

  50. Ogiwara Y, Takahashi K, Kitazawa T and Sakai N 2015 Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter J. Org. Chem. 80 3101

    Article  CAS  PubMed  Google Scholar 

  51. Pippal P and Pratap S P 2017 Calcium Ferrite an Efficient Catalyst for Knoevenagel Condensation (A Green Approach) Orient. J. Chem. 33 1736

    Article  CAS  Google Scholar 

  52. Eshghi H, Damavandi S and Zohuri G H 2011 Efficient One-Pot Synthesis of 2-Amino-4 H -Chromenes Catalyzed by Ferric Hydrogen Sulfate and Zr-Based Catalysts of FI Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 41 1067

    Article  CAS  Google Scholar 

  53. Ghashang M, Mansoor S S and Aswin K 2015 Synthesis and in Vitro Microbiological Evaluation of Novel Series of 8-Hydroxy-2-(2-Oxo-2H-Chromen-3-Yl)-5-Phenyl-3H-Chromeno [2,3-d]Pyrimidin-4(5H)-One Derivatives Catalyzed by Reusable Silica-Bonded N-Propylpiperazine Sulfamic Acid Res. Chem. Intermediat. 41 3117

    Article  CAS  Google Scholar 

  54. Behbahani F K and Mehraban S 2015 Synthesis of 2-Amino-3-Cyano-7-Hydroxy-4H-Chromenes Using L-Proline as a Biocatalyst J. Kor. Chem. Soc. 59 284

    Article  CAS  Google Scholar 

  55. Kidwai M and Poddar R 2008 Transesterification of Chromenes Employing Immobilized Lipase in Ionic Liquids Catal. Lett. 124 311

    Article  CAS  Google Scholar 

  56. Makarem S, Mohammadi A A and Fakhari A R 2008 A Multi-Component Electro-Organic Synthesis of 2-Amino-4H-Chromenes Tetrahedron Lett. 49 7194

    Article  CAS  Google Scholar 

  57. Kundu S K and Bhaumik A 2015 A Triazine-Based Porous Organic Polymer: A Novel Heterogeneous Basic Organocatalyst for Facile One-Pot Synthesis of 2-Amino-4H-Chromenes RSC Adv. 5 32730

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Laboratory of Organic Chemistry, Catalysis, and Environment, Faculty of Science, University Ibn Tofail, PO Box 133, 14000, Kenitra, Morocco

    Soukaina Chehab, Youssef Merroun, Achraf Elhallaoui, Tourya Ghailane, Said Boukhris, Taoufiq Guedira, Rachida Ghailane & Abdelaziz Souizi

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  1. Soukaina Chehab
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  2. Youssef Merroun
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  3. Achraf Elhallaoui
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  4. Tourya Ghailane
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  5. Said Boukhris
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  7. Rachida Ghailane
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  8. Abdelaziz Souizi
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Correspondence to Soukaina Chehab or Abdelaziz Souizi.

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Chehab, S., Merroun, Y., Elhallaoui, A. et al. Catalytic performance of cadmium pyrophosphate in the knoevenagel condensation and one-pot multi-component reaction of chromene derivatives. J Chem Sci 135, 95 (2023). https://doi.org/10.1007/s12039-023-02213-x

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  • DOI: https://doi.org/10.1007/s12039-023-02213-x

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