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CuII Immobolized on the Amidinoglycine Functionalized Magnetic Graphene Oxide Promoted the Alkyl Aminophenols Synthesis

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Abstract

In this study, magnetic graphene oxide was functionalized with N-amidinoglycine as efficient bioligand for the copper ions immobilization. This nanocomposite was characterized using Raman, XRD, FE-SEM, EDX, ICP-OES, VSM and FT-IR analysis. This nanocomposite was showed high catalytic activity in the synthesis of alkyl aminophenols via one-pot Petasis Boron Mannich reaction and simply recovered from the reaction mixture by using an external magnetic field and reused for five catalytic cycle without any pre-activation with acceptable yields.

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References

  • Asadi S, Sedghi R, Heravi MM (2017) Pd Nanoparticles immobilized on supported magnetic GO@PAMPS as an auspicious catalyst for Suzuki-Miyaura coupling reaction. Catal Lett 147:2045–2065

    Article  Google Scholar 

  • Ayaz M, Dietrich J, Hulme C (2011) A novel route to synthesize libraries of quinoxalines via Petasis methodology in two synthetic operations. Tetrahedron Lett 52:4821–4823

    Article  Google Scholar 

  • Berrée F, Debache A, Marsac Y, Collet B, Girard-Le Bleiz P, Carboni B (2006) Stereoselective synthesis of 2-hydroxymorpholines and aminodiols via a three-component boro-Mannich reaction. Tetrahedron 62:4027–4037

    Article  Google Scholar 

  • Candeias NR, Montalbano F, Cal PMSD, Gois PMP (2010) Boronic acids and esters in the petasis-borono mannich multicomponent reaction. Chem Rev 110:6169–6193

    Article  Google Scholar 

  • Chacko P, Shivashankar K (2018) Synthesis of aminomethylphenol derivatives via magnetic nano Fe3O4 catalyzed one pot Petasis borono-Mannich reaction. J Chem Sci 130:154–164

    Article  Google Scholar 

  • Chrzanowska M, Grajewska A, Meissner Z, Rozwadowska M, Wiatrowska I (2012) A concise synthesis of tetrahydroisoquinoline-1-carboxylic acids using a Petasis reaction and Pomeranz–Fritsch–Bobbitt cyclization sequence. Tetrahedron 68:3092–3097

    Article  Google Scholar 

  • Dandia A, Bansal S, Sharma R, Rathore KS, Parewa V (2018) Microwave-assisted nanocatalysis: a CuO NPs/rGO composite as an efficient and recyclable catalyst for the Petasis-borono–Mannich reaction. RSC Adv 8:30280–33028

    Article  Google Scholar 

  • Font D, Heras M, Villalgordo JM (2008) Synthesis of pyrimidinyl arylglycines through subsequent Mitsunobu and Petasis reactions. Tetrahedron 64:5226–5235

    Article  Google Scholar 

  • Fu W, Zhang Z, Zhuang P, Shen J, Ye M (2017) One-pot hydrothermal synthesis of magnetically recoverable palladium/reduced graphene oxide nanocomposites and its catalytic applications in cross-coupling reactions. J Colloid Interface Sci 497:83–92

    Article  Google Scholar 

  • Hummers WS, Offeman RE (1958) Preparation of graphitic oxide. J Am Chem Soc 80:1339-1339

    Article  Google Scholar 

  • Huo X, Liu J, Wang B, Zhang H, Yang Z, She X, Xi P (2013) A one-step method to produce graphene–Fe3O4 composites and their excellent catalytic activities for three-component coupling of aldehyde, alkyne and amine. J Mater Chem A 1:651–656

    Article  Google Scholar 

  • Hwang J, Borgelt L, Wu P (2020) Multicomponent Petasis reaction for the synthesis of functionalized 2-aminothiophenes and thienodiazepines. ACS Comb Sci 22:495–499

    Article  Google Scholar 

  • Jourdan H, Gouhier G, Van Hijfte L, Angibaud P, Piettre SR (2005) On the use of boronates in the Petasis reaction. Tetrahedron Lett 46:8027–8031

    Article  Google Scholar 

  • Kaiser PF, Churches QI, Hutton CA (2007) Organoboron reagents in the preparation of functionalized α-amino acids. Aust J Chem 60:799–810

    Article  Google Scholar 

  • Krishnamoorthy K, Mohan R, Kim SJ (2011) Graphene oxide as a photocatalytic material. Appl Phys Lett 98:244101–244104

    Article  Google Scholar 

  • Kulkarni AM, Pandit KS, Chavan PV, Desai UV, Wadgaonkar PP (2015) Cobalt ferrite nanoparticles: a magnetically separable and reusable catalyst for Petasis-Borono–Mannich reaction. RSC Adv 5:70586–70594

    Article  Google Scholar 

  • Lenci E, Bellini Puglielli R, Bucaletti E, Innocenti R, Trabocchi A (2020) A Glucose-derived α-hydroxy aldehyde for the Petasis reaction: facile access to polyfunctional δ-amino acids. Eur J Org Chem 2020:4227–4234

    Article  Google Scholar 

  • Li Y, Xu MH (2012) Lewis Acid Promoted highly diastereoselective Petasis borono-Mannich reaction: efficient synthesis of optically active β, γ-unsaturated α-amino acids. Org Lett 14:2062–2065

    Article  Google Scholar 

  • McLean NJ, Tye H, Whittaker M (2004) Microwave assisted Petasis boronic-Mannich reactions. Tetrahedron Lett 45:993–995

    Article  Google Scholar 

  • Noushini S, Mahdavi M, Firoozpour L, Moghimi S, Shafiee A, Foroumadi A (2015) Efficient multi-component synthesis of 1,4-benzodiazepine-3,5-diones: a Petasis-based approach. Tetrahedron 71:6272–6275

    Article  Google Scholar 

  • Nun P, Martinez J, Lamaty F (2010) Microwave-assisted neat procedure for the Petasis reaction. Synthesis 12:2063–2068

    Google Scholar 

  • Petasis NA, Boral S (2001) One-step three-component reaction among organoboronic acids, amines and salicylaldehydes. Tetrahedron Lett 42:539–542

    Article  Google Scholar 

  • Petasis NA, Zavialov IA (1997) A new and practical synthesis of α-amino acids from alkenyl boronic acids. J Am Chem Soc 119:445–446

    Article  Google Scholar 

  • Petasis NA, Zavialov IA (1998) Highly stereocontrolled one-step synthesis of anti-β-amino alcohols from organoboronic acids, amines, and α-hydroxy aldehydes. J Am Chem Soc 120:11798–11799

    Article  Google Scholar 

  • Petasis NA, Goodman A, Zavialov IA (1997) A new synthesis of α-arylglycines from aryl boronic acids. Tetrahedron 53:16463–16470

    Article  Google Scholar 

  • Portlock DE, Naskar D, West L, Li M (2002) Petasis boronic acid–Mannich reactions of substituted hydrazines: synthesis of α-hydrazinocarboxylic acids. Tetrahedron Lett 43:6845–6847

    Article  Google Scholar 

  • Potowski M, Esken R, Brunschweiger A (2020) Translation of the copper/bipyridine-promoted Petasis reaction to solid phase-coupled DNA for encoded library synthesis. Bioorg Med Chem 28:115441

    Article  Google Scholar 

  • Prakash GKS, Mandal M, Schweizer S, Petasis NA, Olah GA (2000) A facile stereocontrolled synthesis of anti-α-(trifluoromethyl)-β-amino alcohols. Org Lett 2:3173–3176

    Article  Google Scholar 

  • Rafiee F, Khavari P (2020) One-pot three-component synthesis of propargylamines using an efficient and reusable copper bio-functionalized magnetic graphene oxide nanocomposite. Polyhedron 177:114309–114314

    Article  Google Scholar 

  • Reddy SS, Reddy BRP, Reddy PVG (2015) Chitosan: highly efficient, green, and reusable biopolymer catalyst for the synthesis of alkylaminophenols via Petasis borono–Mannich reaction. Tetrahedron Lett 56:4984–4989

    Article  Google Scholar 

  • Reddy BRP, Reddy PVG, Kumar DP, Reddy BN, Shankar MV (2016) Rapid synthesis of alkylaminophenols via the Petasis borono–Mannich reaction using protonated trititanate nanotubes as robust solid–acid catalysts. RSC Adv 6:14682–14691

    Article  Google Scholar 

  • Rosholm T, Gois PMP, Franzen R, Candeias NR (2015) Glycerol as an efficient medium for the Petasis Borono-Mannich reaction. ChemistryOpen 4:39–46

    Article  Google Scholar 

  • Selander N, Kipke A, Sebelius S, Szabó KJ (2007) Petasis borono-Mannich reaction and allylation of carbonyl compounds via transient allyl boronates generated by palladium-catalyzed substitution of allyl alcohols. An efficient one-pot route to stereodefined α-amino acids and homoallyl alcohols. J Am Chem Soc 129:13723–13731

    Article  Google Scholar 

  • Shi X, Hebrault D, Humora M, Kiesman WF, Peng H, Talreja T, Wang Z, Xin Z (2011) Acceleration of Petasis reactions of salicylaldehyde derivatives with molecular sieves. J Org Chem 77:1154–1160

    Article  Google Scholar 

  • Sim YE, Nwajiobi O, Mahesh S, Cohen RD, Reibarkh MY, Raj M (2020) Secondary amine selective Petasis (SASP) bioconjugation. Chem Sci 11:53–61

    Article  Google Scholar 

  • Stas S, Abbaspour Tehrani K (2007) Lewis acid promoted Mannich type reactions of α, α-dichloro aldimines with potassium organotrifluoroborates. Tetrahedron 63:8921–8931

    Article  Google Scholar 

  • Tong M, Bai X, Meng X, Wang J, Wang T, Zhu X, Mao B (2019) Enantioselective synthesis of α-amino esters through Petasis borono-Mannich multicomponent reaction of potassium trifluoroborate salts. J Chem Res 43:557–564

    Article  Google Scholar 

  • Veerapandian M, Lee MH, Krishnamoorthy K, Yun K (2012) Synthesis, characterization and electrochemical properties of functionalized graphene oxide. Carbon 50:4228–4238

    Article  Google Scholar 

  • Wang Q, Finn MG (2000) 2H-Chromenes from salicylaldehydes by a catalytic Petasis reaction. Org Lett 2:4063–4065

    Article  Google Scholar 

  • Wu P, Givskov M, Nielsen TE (2019) Reactivity and synthetic applications of multicomponent Petasis reactions. Chem Rev 119:11245–11290

    Article  Google Scholar 

  • Yadav JS, Reddy BVS, Lakshmi PN (2007) Ionic liquid accelerated Petasis reaction: a green protocol for the synthesis of alkylaminophenols. J Mol Catal A: Chem 274:101–104

    Article  Google Scholar 

  • Zhao X, Liu X (2015) A novel magnetic NiFe2O4@graphene–Pd multifunctional nanocomposite for practical catalytic application. RSC Adv 5:79548–79555

    Article  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the partial financial support received from the research council of Alzahra University.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Physic-chemistry, Alzahra University, P. O. Box: 1993893973, Vanak, Tehran, Iran

    Fatemeh Rafiee & Somayeh Hosseinvand

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  1. Fatemeh Rafiee
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  2. Somayeh Hosseinvand
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Correspondence to Fatemeh Rafiee.

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Rafiee, F., Hosseinvand, S. CuII Immobolized on the Amidinoglycine Functionalized Magnetic Graphene Oxide Promoted the Alkyl Aminophenols Synthesis. Iran J Sci Technol Trans Sci 45, 503–514 (2021). https://doi.org/10.1007/s40995-020-01051-7

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  • DOI: https://doi.org/10.1007/s40995-020-01051-7

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