Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1, 8-dioxooctahydroxanthenes under solvent-free conditions

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Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1, 8-dioxooctahydroxanthenes under solvent-free conditions

Simin Nazari , Mosadegh Keshavarz , Bahador Karami , Nasir Iravani , Masoumeh Vafaee-Nezhad

Citation: Simin Nazari, Mosadegh Keshavarz, Bahador Karami, Nasir Iravani, Masoumeh Vafaee-Nezhad. Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1, 8-dioxooctahydroxanthenes under solvent-free conditions[J]. Chinese Chemical Letters, 2014, 25(2): 317-320. shu

shu

Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1, 8-dioxooctahydroxanthenes under solvent-free conditions

通讯作者: Mosadegh Keshavarz,

摘要: Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water soluble and can be separated from the products by simple filtration. The filtrate can be evaporated to dryness and recrystallized from cool methanol to give the recovered catalyst. This organocatalyst was used for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions and recycled up to 8 consecutive runs without any losing of its efficiency.

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English

Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1, 8-dioxooctahydroxanthenes under solvent-free conditions

1.
a Department of Chemistry, Sousangerd Branch, Islamic Azad University, Sousangerd 44181-6189, Iran;
2.
b Department of Chemistry, Yasouj University, Yasouj 75918-74831, Iran;
3.
c Department of Chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran 75818-63876, Iran

Corresponding author: Mosadegh Keshavarz,

Received Date: 19 July 2013

Abstract: Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. This catalyst is water soluble and can be separated from the products by simple filtration. The filtrate can be evaporated to dryness and recrystallized from cool methanol to give the recovered catalyst. This organocatalyst was used for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions and recycled up to 8 consecutive runs without any losing of its efficiency.

Key words:

1. [1] A.M. El-Brashy, M. El-Sayed Metwally, F.A. El-Sepai, Spectrophotometric determination of some fluoroquinolone antibacterials by binary complex formation with xanthene dyes, Farmaco 59 (2004) 809-817.[1] A.M. El-Brashy, M. El-Sayed Metwally, F.A. El-Sepai, Spectrophotometric determination of some fluoroquinolone antibacterials by binary complex formation with xanthene dyes, Farmaco 59 (2004) 809-817.
2. [2] K. Chibale, M. Visser, D.V. Schalkwyk, et al., Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents, Tetrahedron 59 (2003) 2289-2296.[2] K. Chibale, M. Visser, D.V. Schalkwyk, et al., Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents, Tetrahedron 59 (2003) 2289-2296.
3. [3] B.B. Bhowmik, P. Ganguly, Photophysics of xanthene dyes in surfactant solution, Spectrochim. Acta 61 (2005) 1997-2003.[3] B.B. Bhowmik, P. Ganguly, Photophysics of xanthene dyes in surfactant solution, Spectrochim. Acta 61 (2005) 1997-2003.
4. [4] C.G. Knight, T. Stephens, Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles, Biochem. J. 258 (1989) 683-689.[4] C.G. Knight, T. Stephens, Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles, Biochem. J. 258 (1989) 683-689.
5. [5] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.[5] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.
6. [6] J. Albadi, M. Keshavarz, M. Abedini, M. Khoshakhlagh, Copper iodide nanoparticles on poly(4-vinylpyridine): a new and efficient catalyst for the synthesis of 1,8- dioxooctahydroxanthenes under solvent-free conditions, J. Chem. Sci. 125 (2013) 295-298.[6] J. Albadi, M. Keshavarz, M. Abedini, M. Khoshakhlagh, Copper iodide nanoparticles on poly(4-vinylpyridine): a new and efficient catalyst for the synthesis of 1,8- dioxooctahydroxanthenes under solvent-free conditions, J. Chem. Sci. 125 (2013) 295-298.
7. [7] M.A. Bigdeli, F. Nemati, G.H. Mahdavinia, H. Doostmohammadi, A series of 1,8- dioxooctahydroxanthenes are prepared using trichloroisocyanuric acid, Chin. Chem. Lett. 20 (2009) 1275-1278.[7] M.A. Bigdeli, F. Nemati, G.H. Mahdavinia, H. Doostmohammadi, A series of 1,8- dioxooctahydroxanthenes are prepared using trichloroisocyanuric acid, Chin. Chem. Lett. 20 (2009) 1275-1278.
8. [8] Z. Zhang, P. Zhang, S.H. Yang, H.J. Wang, J. Deng, Multicomponent, solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives catalyzed by cyanuric chloride, J. Chem. Sci. 122 (2010) 427-432.[8] Z. Zhang, P. Zhang, S.H. Yang, H.J. Wang, J. Deng, Multicomponent, solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives catalyzed by cyanuric chloride, J. Chem. Sci. 122 (2010) 427-432.
9. [9] V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, M. Mahdavi, Highly efficient synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes catalysed by carbon-based solid acid under solvent-free conditions, Synth. Commun. 39 (2009) 4328-4340.[9] V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, M. Mahdavi, Highly efficient synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes catalysed by carbon-based solid acid under solvent-free conditions, Synth. Commun. 39 (2009) 4328-4340.
10. [10] B. Karami, S.J. Hoseini, K. Eskandari, A. Ghasemi, H. Nasrabadi, Synthesis of xanthene derivatives by employing Fe₃O₄ nanoparticles as an effective and magnetically recoverable catalyst in water, Catal. Sci. Technol. 2 (2012) 331-338.[10] B. Karami, S.J. Hoseini, K. Eskandari, A. Ghasemi, H. Nasrabadi, Synthesis of xanthene derivatives by employing Fe₃O₄ nanoparticles as an effective and magnetically recoverable catalyst in water, Catal. Sci. Technol. 2 (2012) 331-338.
11. [11] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23 (2012) 1225-1229.[11] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23 (2012) 1225-1229.
12. [12] J. Mondal, M. Nandi, A. Modak, A. Bhaumik, Functionalized mesoporous materials as efficient organocatalysts for the syntheses of xanthenes, J. Mol. Catal. A: Chem. 363-364 (2012) 254-264.[12] J. Mondal, M. Nandi, A. Modak, A. Bhaumik, Functionalized mesoporous materials as efficient organocatalysts for the syntheses of xanthenes, J. Mol. Catal. A: Chem. 363-364 (2012) 254-264.
13. [13] J. Venu-Madhav, Y. Thirupathi-Reddy, P. Narsimha-Reddy, et al., Cellulose sulfuric acid: an efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions, J. Mol. Catal. A: Chem. 304 (2009) 85-87.[13] J. Venu-Madhav, Y. Thirupathi-Reddy, P. Narsimha-Reddy, et al., Cellulose sulfuric acid: an efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions, J. Mol. Catal. A: Chem. 304 (2009) 85-87.
14. [14] F. Shirini, N. Ghaffari-Khaligh, Succinimide-N-sulfonic acid: an efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions, Dyes Pigments 95 (2012) 789-794.[14] F. Shirini, N. Ghaffari-Khaligh, Succinimide-N-sulfonic acid: an efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions, Dyes Pigments 95 (2012) 789-794.
15. [15] R.Z. Wang, L.F. Zhang, Z.S. Cui, Iodine-catalyzed synthesis of 12-aryl-8,9,10,12- tetrahydro-benzo[a]xanthen-11-one derivatives via multicomponent reaction, Synth. Commun. 39 (2009) 2101-2107.[15] R.Z. Wang, L.F. Zhang, Z.S. Cui, Iodine-catalyzed synthesis of 12-aryl-8,9,10,12- tetrahydro-benzo[a]xanthen-11-one derivatives via multicomponent reaction, Synth. Commun. 39 (2009) 2101-2107.
16. [16] A. Zarei, A.R. Hajipour, L. Khazdooz, The one-pot synthesis of 14-aryl or alkyl-14Hdibenzo[a,j]xanthenes catalyzed by P₂O₅/Al₂O₃ under microwave irradiation, Dyes Pigments 85 (2010) 133-138.[16] A. Zarei, A.R. Hajipour, L. Khazdooz, The one-pot synthesis of 14-aryl or alkyl-14Hdibenzo[a,j]xanthenes catalyzed by P₂O₅/Al₂O₃ under microwave irradiation, Dyes Pigments 85 (2010) 133-138.
17. [17] M. Bigdeli, Clean synthesis of 1,8-dioxooctahydroxanthenes promoted by DABCObromine in aqueous media, Chin. Chem. Lett. 21 (2010) 1180-1182.[17] M. Bigdeli, Clean synthesis of 1,8-dioxooctahydroxanthenes promoted by DABCObromine in aqueous media, Chin. Chem. Lett. 21 (2010) 1180-1182.
18. [18] (a) Special issue about organic catalysis, Adv. Synth. Catal. 346 (9-10) (2004) 1007-1249; (b) Hot Topics, Wiley-VCH, Wurttemberg, 2011, This is a selection of recent articles in field of organocatalyst from Angew. Chem, Chem. Eur. J, Eur. J. Org. Chem and Adv. Synth. Catal..[18] (a) Special issue about organic catalysis, Adv. Synth. Catal. 346 (9-10) (2004) 1007-1249; (b) Hot Topics, Wiley-VCH, Wurttemberg, 2011, This is a selection of recent articles in field of organocatalyst from Angew. Chem, Chem. Eur. J, Eur. J. Org. Chem and Adv. Synth. Catal..
19. [19] T. Okino, Y. Hoashi, Y. Takemoto, Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts, J. Am. Chem. Soc. 125 (2003) 12672-12673.[19] T. Okino, Y. Hoashi, Y. Takemoto, Enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts, J. Am. Chem. Soc. 125 (2003) 12672-12673.
20. [20] M. Kargar, R. Hekmatshoar, A. Mostashari, Z. Hashemi, Efficient and green synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones using imidazol-1-ylacetic acid as a novel, reusable and water-soluble organocatalyst, Catal. Commun. 15 (2011) 123-126.[20] M. Kargar, R. Hekmatshoar, A. Mostashari, Z. Hashemi, Efficient and green synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones using imidazol-1-ylacetic acid as a novel, reusable and water-soluble organocatalyst, Catal. Commun. 15 (2011) 123-126.
21. [21] D. Fang, K. Gong, Z.L. Liu, Synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by acidic ionic liquids in aqueous media, Catal. Lett. 127 (2009) 291-295.[21] D. Fang, K. Gong, Z.L. Liu, Synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by acidic ionic liquids in aqueous media, Catal. Lett. 127 (2009) 291-295.

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