Preparation of pyrano[3,2-c]chromene-3-carbonitriles using ZnO nano-particles: a comparison between the Box–Behnken experimental design and traditional optimization methods
The Box–Behnken experimental design has been applied to establish the optimized conditions for the synthesis of 2-amino-4,5-dihydro-5-oxo-4-phenylpyrano[3,2- c ]chromene-3-carbonitrile over ZnO nano-particles as catalyst. ZnO nano-particles were prepared using the homogeneous precipitation method an...
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| Vydané v: | Reaction kinetics, mechanisms and catalysis Ročník 118; číslo 2; s. 463 - 479 |
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01.08.2016
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| ISSN: | 1878-5190, 1878-5204 |
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| Abstract | The Box–Behnken experimental design has been applied to establish the optimized conditions for the synthesis of 2-amino-4,5-dihydro-5-oxo-4-phenylpyrano[3,2-
c
]chromene-3-carbonitrile over ZnO nano-particles as catalyst. ZnO nano-particles were prepared using the homogeneous precipitation method and 2-amino ethanol as precipitating agent. Three factors, three level Box–Behnken response surface design has been investigated using process parameters such as catalyst (0.05–0.5 mmol), solvent (5–20 mL) and temperature (50–90 °C). The results of the experiments were fitted to two quadratic polynomial models developed using response surface methodology, representing the functional relationship between the time and the yield of products and the experimental parameters. The predicted time and yield for optimal condition is 3.2 h and 94.6 %, respectively. |
|---|---|
| AbstractList | The Box–Behnken experimental design has been applied to establish the optimized conditions for the synthesis of 2-amino-4,5-dihydro-5-oxo-4-phenylpyrano[3,2-
c
]chromene-3-carbonitrile over ZnO nano-particles as catalyst. ZnO nano-particles were prepared using the homogeneous precipitation method and 2-amino ethanol as precipitating agent. Three factors, three level Box–Behnken response surface design has been investigated using process parameters such as catalyst (0.05–0.5 mmol), solvent (5–20 mL) and temperature (50–90 °C). The results of the experiments were fitted to two quadratic polynomial models developed using response surface methodology, representing the functional relationship between the time and the yield of products and the experimental parameters. The predicted time and yield for optimal condition is 3.2 h and 94.6 %, respectively. |
| Author | Ghashang, Majid Baziar, Asma |
| Author_xml | – sequence: 1 givenname: Asma surname: Baziar fullname: Baziar, Asma organization: Department of Chemistry, Shiraz Branch, Islamic Azad University – sequence: 2 givenname: Majid surname: Ghashang fullname: Ghashang, Majid email: ghashangmajid@gmail.com organization: Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University |
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| Cites_doi | 10.3987/R-1987-04-0903 10.2174/1573413710666140923211414 10.1016/S1872-2067(12)60727-X 10.3906/kim-1501-106 10.1080/00401706.1960.10489912 10.1007/s11144-014-0728-9 10.1039/c2md20089a 10.2174/1872210510999151126110657 10.1016/0223-5234(93)90020-F 10.1016/j.arabjc.2015.06.029 10.1533/9780857099785.322 10.1021/cc900101w 10.1039/c2ra01056a |
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| References | Ellis GP (1977) Chapter II. In: Weissberger A, Taylor EC (eds) The chemistry of heterocyclic compounds chromenes, chromanes and chromones. Wiley, New York, pp 11–139 Gardiner WP, Gettinby G (1998) Chapter 11. In: Experimental design techniques in statistical practice: a practical software-based approach. Woodhead Publishing, Chichester, pp 322–354 CristóvãoROAmaralPFFTavaresAPMCoelhoMAZCammarotaMCLoureiroJMBoaventuraRARMacedoEAPessoaFLPOptimization of laccase catalyzed degradation of reactive textile dyes in supercritical carbon dioxide medium by response surface methodologyReac Kinet Mech Cat201099311323 Shankar SinghMChowdhurySRecent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesisRSC Adv201224547459210.1039/c2ra01056a BonsignoreLLoyGSecciDCalignanoASynthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivativesEur J Med Chem1993285175201:CAS:528:DyaK2cXlsVChsw%3D%3D10.1016/0223-5234(93)90020-F AbdouMMEl-SaeedRABondockSRecent advances in 4-hydroxycoumarin chemistry. Part 2: scaffolds for heterocycle molecular diversityArab J Chem2015 KhuriAICornellJAResponse surfaces19962New YorkDekker BoxGEPBehnkenDWSome new three level designs for the study of quantitative variablesTechnometrics1960245547510.1080/00401706.1960.10489912 MoradiGMohadesiMHojabriZBiodiesel production by CaO/SiO2 catalyst synthesized by the sol–gel processReac Kinet Mech Cat20141131691861:CAS:528:DC%2BC2cXovVWrtLs%3D10.1007/s11144-014-0728-9 GhashangMMansoorSSAswinKThiourea dioxide: an efficient and reusable organocatalyst for the rapid one-pot synthesis of pyrano[4,3-b]pyran derivatives in waterChin J Catal2014351271331:CAS:528:DC%2BC2cXpslSks7c%3D10.1016/S1872-2067(12)60727-X LaskarSBrahmachariGAccess to biologically relevant diverse chromene heterocycles via multicomponent reactions (MCRs): recent advancesSignpost Open Access J Org Biomol Chem20142150 AndreaniLLLapiEAspects and orientations of modern pharmacognosyBull Chim Farm196099583586 MobinikhalediAYazdanipourAGhashangMGreen synthesis of 2-amino-7-hydroxy-4-aryl-4H-chromene-3-carbonitriles using ZnO nanoparticles prepared with mulberry leaf extract and ZnCl2Turk J Chem2015396676751:CAS:528:DC%2BC2MXhtlShsLbP10.3906/kim-1501-106 WitteECNeubertPRoeschA7-(Piperazinylpopoxy)-2H-1-benzopyran-2-ones. Ger. Offen DE., 1986; 3427985Chem Abstr1986104224915f HafezEAElnagdiMHElagemeyAGAEl-TaweelFMAANitriles in heterocyclic synthesis: novel synthesis of benzo[c]coumarin and of benzo[c]pyrano[3,2-c]quinoline derivativesHeterocycles1987269039071:CAS:528:DyaL1cXlvVOr10.3987/R-1987-04-0903 Ghashang M, Kargar M, Mohammad Shafiee MR, Mansoor SS, Fazlinia A, Esfandiari H (2015) CuO nanostructures prepared in Rosmarinus officinalis leaves extract medium: efficient catalysts for the aqueous media preparation of dihydropyrano[3,2-c]chromene derivatives. Rec Pat Nanotech 9:204–211 BehmaneshfarAGhashangMMohammad ShafieeMRSaffar-TeluriAFazliniaAEsfandiariHOptimization of the preparation condition of 2,4,5-triphenyl-1H-imidazole over BaSO4 nanoparticles as catalyst using a response surface methodology (RSM)Curr Nanosci20151156631:CAS:528:DC%2BC2MXltVGl10.2174/1573413710666140923211414 SlobbePRuijterEOrruRVARecent applications of multicomponent reactions in medicinal chemistryMed Chem Commun20123118912181:CAS:528:DC%2BC38XhsVWns73L10.1039/c2md20089a Shaabani A, Ghadari R, Ghasemi S, Pedarpour M, Rezayan AH, Sarvary A, Weng Ng S (2009) Novel one-pot three- and pseudo-five-component reactions: synthesis of functionalized benzo[g]- and dihydropyrano[2,3-g]chromene derivatives. J Comb Chem 11:956–959 FoyeWOPrincipi Di Chimica Farmaceutica1991PadovaPiccin416 A Behmaneshfar (1013_CR13) 2015; 11 RO Cristóvão (1013_CR17) 2010; 99 GEP Box (1013_CR15) 1960; 2 AI Khuri (1013_CR14) 1996 P Slobbe (1013_CR9) 2012; 3 L Bonsignore (1013_CR3) 1993; 28 M Shankar Singh (1013_CR10) 2012; 2 A Mobinikhaledi (1013_CR11) 2015; 39 1013_CR20 1013_CR19 1013_CR5 MM Abdou (1013_CR7) 2015 1013_CR16 LL Andreani (1013_CR2) 1960; 99 EA Hafez (1013_CR6) 1987; 26 S Laskar (1013_CR8) 2014; 2 EC Witte (1013_CR4) 1986; 104 G Moradi (1013_CR18) 2014; 113 WO Foye (1013_CR1) 1991 M Ghashang (1013_CR12) 2014; 35 |
| References_xml | – reference: BehmaneshfarAGhashangMMohammad ShafieeMRSaffar-TeluriAFazliniaAEsfandiariHOptimization of the preparation condition of 2,4,5-triphenyl-1H-imidazole over BaSO4 nanoparticles as catalyst using a response surface methodology (RSM)Curr Nanosci20151156631:CAS:528:DC%2BC2MXltVGl10.2174/1573413710666140923211414 – reference: GhashangMMansoorSSAswinKThiourea dioxide: an efficient and reusable organocatalyst for the rapid one-pot synthesis of pyrano[4,3-b]pyran derivatives in waterChin J Catal2014351271331:CAS:528:DC%2BC2cXpslSks7c%3D10.1016/S1872-2067(12)60727-X – reference: Shaabani A, Ghadari R, Ghasemi S, Pedarpour M, Rezayan AH, Sarvary A, Weng Ng S (2009) Novel one-pot three- and pseudo-five-component reactions: synthesis of functionalized benzo[g]- and dihydropyrano[2,3-g]chromene derivatives. J Comb Chem 11:956–959 – reference: Ghashang M, Kargar M, Mohammad Shafiee MR, Mansoor SS, Fazlinia A, Esfandiari H (2015) CuO nanostructures prepared in Rosmarinus officinalis leaves extract medium: efficient catalysts for the aqueous media preparation of dihydropyrano[3,2-c]chromene derivatives. Rec Pat Nanotech 9:204–211 – reference: FoyeWOPrincipi Di Chimica Farmaceutica1991PadovaPiccin416 – reference: BonsignoreLLoyGSecciDCalignanoASynthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivativesEur J Med Chem1993285175201:CAS:528:DyaK2cXlsVChsw%3D%3D10.1016/0223-5234(93)90020-F – reference: Gardiner WP, Gettinby G (1998) Chapter 11. In: Experimental design techniques in statistical practice: a practical software-based approach. Woodhead Publishing, Chichester, pp 322–354 – reference: AbdouMMEl-SaeedRABondockSRecent advances in 4-hydroxycoumarin chemistry. Part 2: scaffolds for heterocycle molecular diversityArab J Chem2015 – reference: MobinikhalediAYazdanipourAGhashangMGreen synthesis of 2-amino-7-hydroxy-4-aryl-4H-chromene-3-carbonitriles using ZnO nanoparticles prepared with mulberry leaf extract and ZnCl2Turk J Chem2015396676751:CAS:528:DC%2BC2MXhtlShsLbP10.3906/kim-1501-106 – reference: LaskarSBrahmachariGAccess to biologically relevant diverse chromene heterocycles via multicomponent reactions (MCRs): recent advancesSignpost Open Access J Org Biomol Chem20142150 – reference: KhuriAICornellJAResponse surfaces19962New YorkDekker – reference: AndreaniLLLapiEAspects and orientations of modern pharmacognosyBull Chim Farm196099583586 – reference: MoradiGMohadesiMHojabriZBiodiesel production by CaO/SiO2 catalyst synthesized by the sol–gel processReac Kinet Mech Cat20141131691861:CAS:528:DC%2BC2cXovVWrtLs%3D10.1007/s11144-014-0728-9 – reference: SlobbePRuijterEOrruRVARecent applications of multicomponent reactions in medicinal chemistryMed Chem Commun20123118912181:CAS:528:DC%2BC38XhsVWns73L10.1039/c2md20089a – reference: BoxGEPBehnkenDWSome new three level designs for the study of quantitative variablesTechnometrics1960245547510.1080/00401706.1960.10489912 – reference: CristóvãoROAmaralPFFTavaresAPMCoelhoMAZCammarotaMCLoureiroJMBoaventuraRARMacedoEAPessoaFLPOptimization of laccase catalyzed degradation of reactive textile dyes in supercritical carbon dioxide medium by response surface methodologyReac Kinet Mech Cat201099311323 – reference: Ellis GP (1977) Chapter II. In: Weissberger A, Taylor EC (eds) The chemistry of heterocyclic compounds chromenes, chromanes and chromones. Wiley, New York, pp 11–139 – reference: WitteECNeubertPRoeschA7-(Piperazinylpopoxy)-2H-1-benzopyran-2-ones. Ger. Offen DE., 1986; 3427985Chem Abstr1986104224915f – reference: Shankar SinghMChowdhurySRecent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesisRSC Adv201224547459210.1039/c2ra01056a – reference: HafezEAElnagdiMHElagemeyAGAEl-TaweelFMAANitriles in heterocyclic synthesis: novel synthesis of benzo[c]coumarin and of benzo[c]pyrano[3,2-c]quinoline derivativesHeterocycles1987269039071:CAS:528:DyaL1cXlvVOr10.3987/R-1987-04-0903 – volume: 26 start-page: 903 year: 1987 ident: 1013_CR6 publication-title: Heterocycles doi: 10.3987/R-1987-04-0903 – start-page: 416 volume-title: Principi Di Chimica Farmaceutica year: 1991 ident: 1013_CR1 – volume: 11 start-page: 56 year: 2015 ident: 1013_CR13 publication-title: Curr Nanosci doi: 10.2174/1573413710666140923211414 – volume: 2 start-page: 1 year: 2014 ident: 1013_CR8 publication-title: Signpost Open Access J Org Biomol Chem – volume: 35 start-page: 127 year: 2014 ident: 1013_CR12 publication-title: Chin J Catal doi: 10.1016/S1872-2067(12)60727-X – volume: 39 start-page: 667 year: 2015 ident: 1013_CR11 publication-title: Turk J Chem doi: 10.3906/kim-1501-106 – volume: 2 start-page: 455 year: 1960 ident: 1013_CR15 publication-title: Technometrics doi: 10.1080/00401706.1960.10489912 – ident: 1013_CR5 – volume: 113 start-page: 169 year: 2014 ident: 1013_CR18 publication-title: Reac Kinet Mech Cat doi: 10.1007/s11144-014-0728-9 – volume: 3 start-page: 1189 year: 2012 ident: 1013_CR9 publication-title: Med Chem Commun doi: 10.1039/c2md20089a – ident: 1013_CR20 doi: 10.2174/1872210510999151126110657 – volume: 99 start-page: 311 year: 2010 ident: 1013_CR17 publication-title: Reac Kinet Mech Cat – volume: 104 start-page: 224915f year: 1986 ident: 1013_CR4 publication-title: Chem Abstr – volume: 28 start-page: 517 year: 1993 ident: 1013_CR3 publication-title: Eur J Med Chem doi: 10.1016/0223-5234(93)90020-F – year: 2015 ident: 1013_CR7 publication-title: Arab J Chem doi: 10.1016/j.arabjc.2015.06.029 – volume: 99 start-page: 583 year: 1960 ident: 1013_CR2 publication-title: Bull Chim Farm – ident: 1013_CR16 doi: 10.1533/9780857099785.322 – volume-title: Response surfaces year: 1996 ident: 1013_CR14 – ident: 1013_CR19 doi: 10.1021/cc900101w – volume: 2 start-page: 4547 year: 2012 ident: 1013_CR10 publication-title: RSC Adv doi: 10.1039/c2ra01056a |
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