2020
DOI: 10.1016/j.cattod.2019.08.002
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Basolites: A type of Metal Organic Frameworks highly efficient in the one-pot synthesis of quinoxalines from α-hydroxy ketones under aerobic conditions

Abstract: We report here efficient synthesis of quinoxalines from ophenylendiamine and -hydroxy ketones over commercial Basolites. The concentration and type of acid centres, as CUS sites, together with the porosity of the samples strongly influence the resulting conversion and selectivity. Our results indicate a new reaction route in which tautomerization reactions are also involved.

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Cited by 11 publications
(8 citation statements)
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“…The E-factor without the inclusion of water for the synthesis of quinoxaline 3aa in 98% yield from 20 mmol of o-phenylenediamine (1a) and 20 mmol of benzoin (2a), 14 mL of EtOH, 60 mL of WEPA and 50 mL of water (calculated from the multigram-scale synthesis of 3aa including product separation and 11 24 Fe exchanged molybdophosphoric acid CH 3 CN Reflux 3 49-99 12 25 FeCl 3 , morpholine EtOH 80 0.3-12 00-96 13 26 Basolite F300 (Fe-BTC) PhMe 100 3-4 5 6 -100 14 27 ZnI 2 EtOH 80 0.5-0.7 84-95 15 28 Zn[L-proline] AcOH RT 0.1-0.3 92-96 16 29 Cu-Mn mixed oxides@hydrotalcite, O 2 EtOH 70 6 82-95 17 30 Polymer-Cu complex, KO t Bu PhMe 90 1-5 6 6 -100 18 30 CuCl 2 , 4 Å molecular sieves PhMe 120 12 65-91 19 31 CuCl 2 PhMe 100 32 72-95 20 32 Sulfated polyborate -100 0.1-0.2 95-99 21 9 Amberlite IR-120H -110 5 82-96 22 33 T 3 P DMSO, EtOAc 0 to 25 5-6 9 0 -95 The E-factor with the inclusion of water for the synthesis of quinoxaline 3aa in 98% yield from 20 mmol of o-phenylenediamine (1a) and 20 mmol of benzoin (2a), 14 mL of EtOH, 60 mL of WEPA and 50 mL of water: E-factor = {[2.16 g of 1a + 4.24 g of 2a + 11.05 g of EtOH + 0.13 + 110 g of water] -(5.53 g of quinoxaline, 3aa + 7.39 g of recovered EtOH + 83.60 g of recovered water)}/5.53 g of quinoxaline 3aa = 5.62.…”
Section: Calculation Of the E-factormentioning
confidence: 99%
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“…The E-factor without the inclusion of water for the synthesis of quinoxaline 3aa in 98% yield from 20 mmol of o-phenylenediamine (1a) and 20 mmol of benzoin (2a), 14 mL of EtOH, 60 mL of WEPA and 50 mL of water (calculated from the multigram-scale synthesis of 3aa including product separation and 11 24 Fe exchanged molybdophosphoric acid CH 3 CN Reflux 3 49-99 12 25 FeCl 3 , morpholine EtOH 80 0.3-12 00-96 13 26 Basolite F300 (Fe-BTC) PhMe 100 3-4 5 6 -100 14 27 ZnI 2 EtOH 80 0.5-0.7 84-95 15 28 Zn[L-proline] AcOH RT 0.1-0.3 92-96 16 29 Cu-Mn mixed oxides@hydrotalcite, O 2 EtOH 70 6 82-95 17 30 Polymer-Cu complex, KO t Bu PhMe 90 1-5 6 6 -100 18 30 CuCl 2 , 4 Å molecular sieves PhMe 120 12 65-91 19 31 CuCl 2 PhMe 100 32 72-95 20 32 Sulfated polyborate -100 0.1-0.2 95-99 21 9 Amberlite IR-120H -110 5 82-96 22 33 T 3 P DMSO, EtOAc 0 to 25 5-6 9 0 -95 The E-factor with the inclusion of water for the synthesis of quinoxaline 3aa in 98% yield from 20 mmol of o-phenylenediamine (1a) and 20 mmol of benzoin (2a), 14 mL of EtOH, 60 mL of WEPA and 50 mL of water: E-factor = {[2.16 g of 1a + 4.24 g of 2a + 11.05 g of EtOH + 0.13 + 110 g of water] -(5.53 g of quinoxaline, 3aa + 7.39 g of recovered EtOH + 83.60 g of recovered water)}/5.53 g of quinoxaline 3aa = 5.62.…”
Section: Calculation Of the E-factormentioning
confidence: 99%
“…In connection with their high biological and materialistic significance, several strategies have been developed for quinoxaline synthesis and most of them consist of a common condensation route of organic 1,2-diamines with other organic substances, including 1,2-diketones, 14 1,2-diols, 15 α-hydroxy ketones 8,9,16–35 and alkynes. 36 Among these strategies, the reaction of organic 1,2-diamines with α-hydroxy ketones or alkynes is relatively less explored, and requires metal-based catalysts/oxidizing agents or non-renewable catalysts under harsh reaction conditions.…”
Section: Introductionmentioning
confidence: 99%
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“…At this respect, we reported exper-imental and theoretical studies concerning the synthesis of quinolines via Friedländer reaction catalyzed by Cu 3 (BTC) 2 [13][14][15][16]. Much more recently, commercial Basolites, particularly C300, F300 and Z1200, have been proposed by some of us as efficient porous catalytic active systems in the synthesis of important heterocyclic scaffolds such as quinoxalines [17].…”
Section: Introductionmentioning
confidence: 99%