Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

One-pot Synthesis of Tetrahydrobenzo[b]pyrans and Pyranopyrazoles Tetrahydrochromenochromene by Ammonium Fluoride

Document Type : Research Article

Authors
Matin Asadi
Sepideh Ehsanifar
Masoud Mokhtary
Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, I.R. IRAN
Abstract
Consideration for the development of new methods for the efficient preparation of heterocyclic compounds is an important issue in the synthesis of organic compounds in chemistry. The benzo[b]pyrans and pyranopyrazoles are important heterocyclic compounds that constitute the structural unit of a series of important natural biological products. In this research, ammonium fluoride was successfully applied to perform a one-pot reaction of aryl aldehydes, dimedone, or 1,3-cyclohexadione and malononitrile in EtOH:H2O (1:1) at room temperature to provide a series of tetrahydrobenzo[b]pyrans in excellent yields. Furthermore, ammonium fluoride catalyzed four-component condensations of aldehyde, malononitrile, hydrazine hydrate, and ethyl acetoacetate to synthesize pyranopyrazole derivatives in EtOH:H2O (1:1) at 80 °C. Clean methodologies, short reaction time, high yields, cost-effective catalysts, non-toxic, and environmentally friendly solvent are some advantages of this research. All products were characterized by spectral data and by comparison with authentic samples reported in the literature.
Keywords
Tetrahydrobenzo[b]pyran
Pyranopyrazole؛ Ammonium fluoride؛ Malononitrile؛ One-pot synthesis

Subjects

[1] Bonsignore L., Loy G., Secci D., Calignano A. Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives. Eur. J. Med. Chem., 28: 517-520 (1993).
[2] Saini, A.; Kumar, S.; Sandhu, J.S.; A new LiBr-catalyzed, facile and efficient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes and tetrahydrobenzo[b]pyrans under solvent-free conventional and microwave heating, Synlett, 1928-1932 (2006).
[3] Hatakeyama S., Ochi N., Numata H., Takano S. A new route to substituted 3-methoxycarbonyldihydropyrans; enantioselective synthesis of (–)-methyl elenolate. J. Chem. Soc. Chem. Commun., 21: 1202-1204 (1988).
[4] Nimbalkar U. D., Seijas, J. A., Vazquez-Tato M. P., Damale M. G., Sangshetti J. N.,  Nikalje A. P. G. Ionic liquid-catalyzed green protocol for multi-component synthesis of dihydropyrano[2,3-c]pyrazoles as potential anticancer scaffolds. Molecules,  22: 1628-1645 (2017).
[5] Zaki M. E. A., Saliman H. A., Hiekal O. A., Rashad A. E. Z.,Pyrazolopyranopyrimidines as a class of anti-inflammatory agents. Naturforsch. C: Biosci., 61: 1- 5 (2006).
[6] Foloppe N., Fisher L. M., Howes R., Potter A., Robertson A. G., Surgenor A. E. Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening. Bioorg. Med. Chem.,14: 4792-4802 (2006).
[7] Alizadeh A., Khodaei M. M., Beygzadeh M., Kordestani D., Feyzi M., Biguanide-Functionalized Fe3O4/SiO2 Magnetic Nanoparticles: An Efficient Heterogeneous Organosuperbase Catalyst for Various Organic Transformations in Aqueous Media. Bull. Korean Chem. Soc.,33: 2546-2552 (2012).
[8] Abdollahi-Alibeik M., Nezampour F. Synthesis of 4H-benzo[b]pyrans in the presence of sulfated MCM-41 nanoparticles as efficient and reusable solid acid catalyst. Reac. Kinet. Mech. Cat., 108: 213-229 (2013).
[9] Hasaninejad A., Shekouhy M., Golzar N., Zare A., Doroodmand M. M. Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H-benzo[b]pyran derivatives. Appl. Catal. A Gen., 402:11-22 (2011).
[10] Shi D., Mou J., Zhuang Q., Wang X., One-pot synthesis of 2-amino-4-aryl-5-oxo-5,6,7,8-tetrahydro-4H-1-benzopyran-3-carbonitriles in aqueous media. J. Chem. Res., 821-823 (2004).
[11 Mohammadi Ziarani, G.; Abbasi, A.; Badiei, A.; Aslani, Z.; An efficient synthesis of tetrahydrobenzo[b]pyran derivatives using sulfonic acid functionalized silica as an efficient catalyst. J. Chem., 8: 293-299 (2011).
[12] Shirini F., Abedini M., Zarrabzadeh S., Seddighi M. Efficient synthesis of 4H-pyran derivatives using a polymeric catalyst based on PVP. J. Iran. Chem. Soc. 12: 2105-2113 (2015).
[13] Chen L.,  Bao S.,  Yang L., Zhang X., Li B., Li Y. Cheap thiamine hydrochloride as efficient catalyst for synthesis of 4H-benzo[b]pyrans in aqueous ethanol. Res. Chem. Intermed., 43: 3883-3891(2017).
[14] Sharma P., Gupta M., Kant R., Gupta V. K., One-pot synthesis of various 2-amino-4H-chromene derivatives using a highly active supported ionic liquid catalyst. RSC Adv., 6: 32052-32059 (2016).
[15] Pore D. M., Undale  K. A., Dongare  B. B., Desai U. V. Potassium Phosphate Catalyzed a Rapid Three-Component Synthesis of Tetrahydrobenzo[b]pyran at Ambient Temperature. Catal. Lett., 132: 104-108 (2009).
[16] Azarifar D., Abbasi Y. Sulfonic acid–functionalized magnetic Fe3-xTixO4 nanoparticles: New recyclable heterogeneous catalyst for one-pot synthesis of tetrahydrobenzo[b]pyrans and dihydropyrano[2,3-c]pyrazole derivatives. Synth. Commun., 46: 745-758 (2016).
[17] Jin T. S., Wang A. Q., Shi F., Han L. S., Liu L. B., Li T. S. Hexadecyldimethyl benzyl ammonium bromide: an efficient catalyst for a clean one-pot synthesis of tetrahydrobenzopyran derivatives in water.ARKIVOC, xiv: 78-86 (2006).
[18] Moosavi-Zare A. R., Zolfigol M. A., Noroozizadeh E., Tavasoli M., Khakyzadeh V., Zare A. Synthesis of 6-amino-4-(4-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazoles using disulfonic acid imidazolium chloroaluminate as a dual and heterogeneous catalyst. New J. Chem., 37:4089-4094 (2013).
[19] Kiyani H., Samimi H. A., Ghorbani F., Esmaieli S. One-pot, four-component synthesis of pyrano[2,3-c]pyrazoles catalyzed by sodium benzoate in aqueous medium. Curr. Chem. Lett. 2: 197-206 (2013).
[20] Brahmachari G., Banerjee B., Room temperature one-pot green synthesis of coumarin-3-carboxylic acids in water: a practical method for the large-scale synthesis. ACS Sust. Chem. Eng., 2: 411-422 (2014).
[21] Zhou C. F., Li J. J., Su W. K.. Morpholine triflate promoted one-pot, four-component synthesis of dihydropyrano[2,3-c]pyrazoles. Chin. Chem. Lett., 27: 1686-1690 (2016).
[22] Kumar G. S., Kurumurthy C., Veeraswamy B., Rao P. S., Rao P. S., Narsaiah B. An efficient multi-component synthesis of 6-amino-3-methyl-4-Aryl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles. Org. Prep. Proced. Int., 45: 429-436 (2013).
[23] Soleimani E., Jafarzadeh M., Norouzi P., Dayou J., Sipaut C. S., Mansa R. F., Saei P. Synthesis of pyranopyrazoles using magnetically recyclable heterogeneous iron oxide-silica core-shell nanocatalyst. J. Chin. Chem. Soc. 62: 1155-1162 (2015).
[24] Mecadon H., Rohman M. R., Rajbangshi M., Myrboh B. γ-Alumina as a recyclable catalyst for the four-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in aqueous medium.Tetrahedron Lett., 52: 2523-2525 (2011).
[25] Mecadon H., Rohman M. R., Kharbangar I., Laloo B. M., Kharkongor I., Rajbangshi  M., Myrboh B. l-Proline as an efficicent catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles in water.Tetrahedron Lett., 52: 3228-3231 (2011).
[26] Tayade Y. A., Padvi S. A., Wagh Y. B., Dalal D. S. β-Cyclodextrin as a supramolecular catalyst for the synthesis of dihydropyrano[2,3-c]pyrazole and spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] in aqueous medium.Tetrahedron Lett., 56: 2441-2447 (2015).
[27] Wu M., Feng Q., Wan H. D., Ma J. CTACl as catalyst for four-component, one-pot synthesis of pyranopyrazole derivatives in aqueous medium. Synth. Commun., 43: 1721-1726 (2013).
[28] Atar, A.B.; Kim, J.T.; Lim, K.T.; Jeong, Y.T.; Synthesis of 6-amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles catalyzed by silica-supported tetramethylguanidine under solvent-free conditions. Synth. Commun., 44: 2679-2691 (2014).
[29] Vekariya, R. H.; Patel, K.D.; Patel, H.; Fruit juice of Citrus limon as a biodegradable and reusable catalyst for facile, eco-friendly and green synthesis of 3,4-disubstituted isoxazol-5(4H)-ones and dihydropyrano[2,3-c]-pyrazole derivatives. Res. Chem. Intermed., 42: 4683-4696 (2016).
[30] Khurana J. M., Chaudhary A., Efficient and green synthesis of 4H-pyrans and 4H-pyrano[2,3-c] pyrazoles catalyzed by task-specific ionic liquid [bmim]OH under solvent-free conditions. Green Chem. Lett. Rev., 5: 633-638 (2012).
[31] Sachdeva H., Saroj R.,ZnO nanoparticles as an efficient, heterogeneous, reusable, and ecofriendly catalyst for four-component one-pot green synthesis of pyranopyrazole derivatives in water. Sci. World. J.,(2013).
[32] Reddy, G.M.; Garcia, J.R.; Synthesis of pyranopyrazoles under eco-friendly approach by using acid catalysis. J. Heterocyclic Chem., 54: 89-94 (2017).
[33]  Maleki, B.; Eshghi, H, Barghamadi, M.; Nasiri, N.; Khojastehnezhad, A.; Ashrafi, S.S.; Pourshiani, O. Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives. Res. Chem. Intermed., 42: 3071–3093 (2016).
[34] Maleki, B.; Nasiri, N.; Tayebee, R.; Khojastehnezhad, A.; Akhlaghi H.A. Green synthesis of tetrahydrobenzo[b]pyrans, pyrano[2,3-c]pyrazoles and spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles catalyzed by nano-structured diphosphate in water., RSC Adv., 6: 79128-79134 (2016).
[35] Maghsoodlou M. T., Heydari R., Mohamadpour F.Fe2O3 as an environmentally benign natural catalyst for one-pot and solvent-free synthesis of spiro-4H-pyran derivatives. Iran. J. Chem. Chem. Eng.,36: 31-38 (2017).