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Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

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Abstract

A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the three-component tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50 °C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in α,β-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyran-annulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

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References

  1. Y.M. Litvinov, V.Y. Mortikov, A.M. Shestopalov, J. Comb. Chem. 10, 741 (2008)

    Article  CAS  Google Scholar 

  2. M.S. Singh, S. Chowdhury, RSC Adv. 2, 4547 (2012)

    Article  CAS  Google Scholar 

  3. K. Wang, K. Nguyen, Y. Huang, A. Dömling, J. Comb. Chem. 11, 920 (2009)

    Article  CAS  Google Scholar 

  4. J.-P. Wan, Y. Liu, RSC Adv. 2, 9763 (2012)

    Article  CAS  Google Scholar 

  5. A. Dömling, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)

    Article  CAS  Google Scholar 

  6. C. Graaff, E. Ruijter, R.V.A. Orru, Chem. Soc. Rev. 41, 3969 (2012)

    Article  CAS  Google Scholar 

  7. B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Chem. Rev. (2014). doi:10.1021/cr400615v

  8. N.R. Candeias, P.M.S.D. Cal, V. Andre, M.T. Duarte, L.F. Veiros, P.M.P. Gois, Tetrahedron 66, 2736 (2010)

    Article  CAS  Google Scholar 

  9. K. Kumaravel, G. Vasuki, Curr. Org. Chem. 13, 1820 (2009)

    Article  CAS  Google Scholar 

  10. A. Chanda, V.V. Fokin, Chem. Rev. 109, 725 (2009)

    Article  CAS  Google Scholar 

  11. Y. Gu, Green Chem. 14, 2091 (2012)

    Article  CAS  Google Scholar 

  12. R.N. Butler, A.G. Coyne, Chem. Rev. 110, 6302 (2010)

    Article  CAS  Google Scholar 

  13. J. Poupaert, P. Carato, E. Colacino, Curr. Med. Chem. 12, 877 (2005)

    Article  CAS  Google Scholar 

  14. H.G. Kathrotiya, M.P. Patel, Med. Chem. Res. 21, 3406 (2012)

    Article  CAS  Google Scholar 

  15. L. Alvey, S. Prado, B. Saint-Joanis, S. Michel, M. Koch, S.T. Cole, F. Tillequin, Y.L. Janin, Eur. J. Med. Chem. 44, 2497 (2009)

    Article  CAS  Google Scholar 

  16. M. Kidwai, S. Saxena, M.K.R. Khan, S.S. Thukral, Bioorg. Med. Chem. Lett. 15, 4295 (2005)

    Article  CAS  Google Scholar 

  17. T. Symeonidis, M. Chamilos, D.J. Hadjipavlou-Litina, M. Kallitsakis, K.E. Litinas, Bioorg. Med. Chem. Lett. 19, 1139 (2009)

    Article  CAS  Google Scholar 

  18. T. Narender, Shweta, S. Gupta, Bioorg. Med. Chem. Lett. 14, 3913 (2004)

    Article  CAS  Google Scholar 

  19. K. Mansouri, R. Khodarahmi, A. Foroumadi, A. Mostafaie, H. Mohammadi Motlagh, Med. Chem. Res. 20, 920 (2011)

    Article  CAS  Google Scholar 

  20. M. Longobardi, A. Bargagna, E. Mariani, P. Schenone, E. Marmo, IL Farm. 45, 399 (1990)

    CAS  Google Scholar 

  21. K. Görlitzer, A. Dehne, E. Engler, Arch. Pharm. Weinh. Ger. 317, 526 (1983)

    Article  Google Scholar 

  22. P. Coudert, J.M. Coyquelet, J. Bastide, Y. Marion, J. Fialip, Ann. Pharm. Fr. 46, 91 (1988)

    CAS  Google Scholar 

  23. C. Bruhlmann, F. Ooms, P. Carrupt, B. Testa, M. Catto, F. Leonetti, C. Altomare, A. Cartti, J. Med. Chem. 44, 3195 (2001)

    Article  CAS  Google Scholar 

  24. S.R. Kesten, T.G. Heffner, S.J. Johnson, T.A. Pugsley, J.L. Wright, D.L. Wise, J. Med. Chem. 42, 3718 (1999)

    Article  CAS  Google Scholar 

  25. G.P. Ellis, in The Chemistry of Heterocyclic of Compounds. Chromenes, Harmones and Chromones, ed. by A. Weissberger, EC Taylor (Wiley, New York, 1977), Chapter II, pp. 11–13

  26. E.A.A. Hafez, M.H. Elnagdi, A.G.A. Elagamey, F.M.A.A. El-Taweel, Heterocycles 26, 903 (1987)

    Article  CAS  Google Scholar 

  27. G.A. Reynolds, K.H. Drexhage, Opt. Commun. 13, 222 (1975)

    Article  CAS  Google Scholar 

  28. W. Kemnitzer, S. Kasibhatla, S. Jiang, H. Zhang, J. Zhao, S. Jia, L. Xu, C. Crogan-Grundy, R. Denis, N. Barriault, L. Vaillancourt, S. Charron, J. Dodd, G. Attardo, D. Labrecque, S. Lamothe, H. Gourdeau, B. Tseng, J. Drewe, S.X. Cai, Bioorg. Med. Chem. Lett. 15, 4745 (2005)

    Article  CAS  Google Scholar 

  29. W. Kemnitzer, J. Drewe, S. Jiang, H. Zhang, Y. Wang, J. Zhao, S. Jia, J. Herich, D. Labreque, R. Storer, K. Meerovitch, D. Bouffard, R. Rej, R. Denis, C. Blais, S. Lamothe, G. Attardo, H. Gourdeau, B. Tseng, S. Kasibhatla, S.X. Cai, J. Med. Chem. 47, 6299 (2004)

    Article  CAS  Google Scholar 

  30. N. Foloppe, M. Fisher, R. Howes, A. Potter, A.G.S. Robertson, A.E. Surgenor, Bioorg. Med. Chem. 14, 4792 (2006)

    Article  CAS  Google Scholar 

  31. S.X. Cai, J. Drewe, W. Kemnitzer, Anti-Cancer Agents Med. Chem. 9, 437 (2009)

    Article  CAS  Google Scholar 

  32. G.P. Ellis, The Chemistry of Heterocyclic Compounds. in Chromenes, Chromanes, and Chromones, ed. by A. Taylor, EC Weissberger (Wiley, New York, 1977), Chapter II

  33. M.A. Sofan, M.A. El-Taweel, M.H. Elnagdi, Liebigs Ann. Chem. 1989, 935 (1989)

  34. F.M. Abdel Galil, B.Y. Riad, S.M. Sherif, M.H. Elnagdi, Chem. Lett. 11, 1123 (1982)

  35. R.S. Varma, R. Dahiya, J. Org. Chem. 63, 8038 (1998)

    Article  CAS  Google Scholar 

  36. D. Kumar, V.B. Reddy, S. Sharad, U. Dube, S. Kapur, Eur. J. Med. Chem. 44, 3805 (2009)

    Article  CAS  Google Scholar 

  37. J.L. Wang, D.X. Liu, Z.J. Zhang, S.M. Shan, X.B. Han, S.M. Srinivasula, C.M. Croce, E.S. Alnemri, Z.W. Huang, Proc. Natl. Acad. Sci. USA 97, 7124 (2000)

    Article  CAS  Google Scholar 

  38. S.J. Mountford, A.L. Albiston, W.N. Charman, L. Ng, J.K. Holien, M.W. Parker, J.A. Nicolazzo, P.E. Thompson, S.Y. Chai, J. Med. Chem. 57, 1368 (2014)

    Article  CAS  Google Scholar 

  39. T.H.V. Huynh, B. Abrahamsen, K.K. Madsen, A. Gonzalez-Franquesa, A.A. Jensen, L. Bunch, Bioorg. Med. Chem. 20, 6831 (2012)

    Article  CAS  Google Scholar 

  40. H.J. Wang, J. Lu, Z.H. Zhang, Monatsh. Chem. 141, 1107 (2010)

    Article  CAS  Google Scholar 

  41. M.M. Heravi, K. Bakhtiari, V. Zadsirjan, F.F. Bamoharram, O.M. Heravi, Bioorg. Med. Chem. Lett. 17, 4262 (2007)

    Article  CAS  Google Scholar 

  42. S. Abdolmohammadi, S. Balalaie, Tetrahedron Lett. 48, 3299 (2007)

    Article  CAS  Google Scholar 

  43. J.M. Khurana, B. Nand, P. Saluja, Tetrahedron 66, 5637 (2010)

    Article  CAS  Google Scholar 

  44. C.B. Sangani, D.C. Mungra, M.P. Patel, R.G. Patel, Cent. Eur. J. Chem. 9, 635 (2011)

    CAS  Google Scholar 

  45. A.M. El-Agrody, H.S.M. Abd-Rabboh, A.M. Al-Ghamdi, Med. Chem. Res. 22, 1339 (2013)

    Article  CAS  Google Scholar 

  46. A.M. El-Agrody, A.M. Fouda, E.S.A.E.H. Khattab, Med. Chem. Res. 22, 6105–6120 (2013). doi:10.1007/s00044-013-0602-8

    Article  CAS  Google Scholar 

  47. A.M. El-Agrody, A.M. Fouda, A.A.M. Al-Dies, Med. Chem. Res. (2014). doi:10.1007/s00044-013-0904-x

  48. J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)

    Article  CAS  Google Scholar 

  49. A. Shaabani, S. Samadi, Z. Badri, A. Rahmati, Catal. Lett. 104, 39 (2005)

    Article  CAS  Google Scholar 

  50. M.M. Heravi, M. Zakeri, N. Mohammadi, Chin. J. Chem. 29, 1163 (2011)

    Article  CAS  Google Scholar 

  51. A.T. Khan, M. Lal, S. Ali, M.D. Khan, Tetrahedron Lett. 52, 5327 (2011)

    Article  CAS  Google Scholar 

  52. G. Brahmachari, B. Banerjee, ACS Sustain Chem. Eng. 2, 411–422 (2014). doi:10.1021/sc400312n

    Article  CAS  Google Scholar 

  53. H.R. Shaterian, A.R. Oveisi, J. Iran. Chem. Soc. 8, 545 (2011)

    Article  CAS  Google Scholar 

  54. K. Niknam, A. Jamali, Chin. J. Catal. 33, 1840 (2012)

    Article  CAS  Google Scholar 

  55. T.S.R. Prasanna, K.M. Raju, J. Korean Chem. Soc. 55, 662 (2011)

    Article  CAS  Google Scholar 

  56. G. Mohammadi Ziarani, A. Badiei, M. Azizi, P. Zarabadi, Iran. J. Chem. Chem. Eng. 30, 59 (2011)

    CAS  Google Scholar 

  57. H.R. Shaterian, M. Honarmand, Synth. Commun. 41, 3573 (2011)

    Article  CAS  Google Scholar 

  58. H. Nagabhushan, S.S. Saundalkar, L. Muralidhar, B.M. Nagabhushana, C.R. Girija, D. Nagaraja, M.A. Pasha, V.P. Jayashankara, Chin. Chem. Lett. 22, 143 (2011)

    Article  CAS  Google Scholar 

  59. H.R. Shaterian, F. Rigi, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1145-9

    Google Scholar 

  60. N. Hazeri, M.T. Maghsoodlou, M.R. Mousavi, J. Aboonajmi, M. Safarzaei, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1179-z

    Google Scholar 

  61. R.-Y. Guo, Z.-M. An, L.-P. Mo, R.-Z. Wang, H.-X. Liu, S.-X. Wang, Z.-H. Zhang, ACS Comb. Sci. 15, 557 (2013)

    Article  CAS  Google Scholar 

  62. Y.M. Ren, C. Cai, Catal. Commun. 9, 1017 (2008)

    Article  CAS  Google Scholar 

  63. T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, Ultrason. Sonochem. 11, 393 (2004)

    CAS  Google Scholar 

  64. J. Safari, Z. Zarnegar, M. Heydarian, J. Taibah Univ. Sci. 7, 17 (2013)

    Article  Google Scholar 

  65. A. Solhy, A. Elmakssoudi, R. Tahir, M. Karkouri, M. Larzek, M. Bousmina, M. Zahouily, Green Chem. 12, 2261 (2010)

    Article  CAS  Google Scholar 

  66. D. Zhou, Z. Ren, J. Chen, W. Cao, H. Deng, J. Heterocycl. Chem. 45, 1865 (2008)

    Article  CAS  Google Scholar 

  67. M.R. Naimi-Jamal, S. Mashkouri, A. Sharifi, Mol. Divers. 14, 473 (2010)

    Article  CAS  Google Scholar 

  68. J. Mondal, A. Modak, M. Nandi, H. Uyama, A. Bhaumik, RSC Adv. 2, 11306 (2012)

    Article  CAS  Google Scholar 

  69. Z.Q. Zhou, F. Yang, L. Wu, A. Zhang, Chem. Sci. Trans. 1, 57 (2012)

    Article  CAS  Google Scholar 

  70. S.R. Kale, S.S. Kahandal, A.S. Burange, M.B. Gawande, R.V. Jayaram, Catal. Sci. Technol. 3, 2050 (2009)

    Article  CAS  Google Scholar 

  71. M. Bihani, P.P. Bora, G. Bez, H. Askari, C. R. Chim. 16, 419 (2013)

    Article  CAS  Google Scholar 

  72. S. Shinde, G. Rashinkar, R. Salunkhe, J. Mol. Liq. 178, 122 (2013)

    Article  CAS  Google Scholar 

  73. S. Samantaray, D.K. Pradhan, G. Hota, B.G. Mishra, Chem. Eng. J. 193–194, 1 (2012)

    Article  CAS  Google Scholar 

  74. G. Sabitha, M. Bhikshapathi, S. Nayak, R. Srinivas, J.S. Yadav, J. Heterocycl. Chem. 48, 267 (2011)

    Article  CAS  Google Scholar 

  75. H. Mehrabi, N. Kamali, J. Iran. Chem. Soc. 9, 599 (2012)

    Article  CAS  Google Scholar 

  76. E. Mosaddegh, Ultrason. Sonochem. 20, 1436 (2013)

    Article  CAS  Google Scholar 

  77. R. Maggi, R. Ballini, G. Sartori, R. Sartorio, Tetrahedron Lett. 45, 2297 (2004)

    Article  CAS  Google Scholar 

  78. K. Gong, H.-L. Wang, J. Luo, Z.-L. Liu, J. Heterocycl. Chem. 46, 1145 (2009)

    Article  CAS  Google Scholar 

  79. J.M. Khurana, A. Chaudhary, Green Chem. Lett. Rev. 5, 633 (2012)

    Article  CAS  Google Scholar 

  80. W.B. Sun, P. Zhang, J. Fan, S.H. Chen, Z.H. Zhang, Synth. Commun. 40, 587 (2010)

    Article  CAS  Google Scholar 

  81. B. Datta, M.A. Pasha, Ultrason. Sonochem. 19, 725 (2012)

    Article  CAS  Google Scholar 

  82. S. Banerjee, A. Horn, A. Khatri, G. Sereda, Tetrahedron Lett. 52, 1878 (2011)

    Article  CAS  Google Scholar 

  83. C.N. Revanna, T.R. Swaroop, G.M. Raghavendra, D.G. Bhadregowda, K. Mantelingu, K.S. Rangappa, J. Heterocycl. Chem. 49, 851 (2012)

    Article  CAS  Google Scholar 

  84. A. Molla, E. Hossain, S. Hussain, RSC Adv. 3, 21517 (2013)

    Article  CAS  Google Scholar 

  85. S.M. Baghbanian, N. Rezaei, H. Tashakkorian, Green Chem. 15, 3446 (2013)

    Article  CAS  Google Scholar 

  86. J. Davarpanah, A.R. Kiasat, RSC Adv. 4, 4403 (2014)

    Article  CAS  Google Scholar 

  87. M.N. Khan, S. Pal, S. Karamthulla, L.H. Choudhury, RSC Adv. 4, 3732 (2014)

    Article  CAS  Google Scholar 

  88. S.K. Kundu, J. Mondal, A. Bhaumik, Dalton Trans. 42, 10515 (2013)

    Article  CAS  Google Scholar 

  89. A. Fallah-Shojaei, K. Tabatabaeian, F. Shirini, S.Z. Hejazi, RSC Adv. 4, 9509 (2014)

    Article  CAS  Google Scholar 

  90. J.K. Rajput, G. Kaur, Catal. Sci. Technol. 4, 142 (2014)

    Article  CAS  Google Scholar 

  91. R. Sangsuwan, S. Sangher, T. Aree, C. Mahidol, S. Ruchirawatabd, P. Kittakoop, RSC Adv. 4, 13708 (2014)

    Article  CAS  Google Scholar 

  92. J. Safari, Z. Zarnegar, J. Mol. Struct. 1072, 53 (2014)

    Article  CAS  Google Scholar 

  93. N. Hazeri, M.Ta Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35, 391 (2014)

    Article  CAS  Google Scholar 

  94. S. Kanakaraju, B. Prasanna, S. Basavoju, G.V.P. Chandramouli, Arab. J. Chem. (2013). doi: 10.1016/j.arabjc.2013.10.014

  95. V.M. Joshi, R.L. Magar, P.B. Throat, S.U. Tekale, B.R. Patil, M.P. Kale, R.P. Pawar, Chin. Chem. Lett. 25, 455 (2014)

    Article  CAS  Google Scholar 

  96. M.E. Sedaghat, M. Rajabpour Booshehri, M.R. Nazarifar, F. Farhadi, Appl. Clay Sci. 95, 55 (2014)

    Article  CAS  Google Scholar 

  97. M. Mirza-Aghayan, S. Nazmdeh, R. Boukherroub, M. Rahimifard, A.A. Tarlani, M. Abolghasemi-Malakshah, Synth. Commun. 43, 1499 (2013)

    Article  CAS  Google Scholar 

  98. T.M.V.D. Pinho e Melo, Curr. Org. Chem. 9, 925 (2005)

  99. L. Carlsen, D. Dopp, H. Dopp, F. Duus, H. Hartmann, S. Lang-Fugmann, B. Schulze, R.K. Smalley, B.J. Wakefield, in Houben-Weyl, Methods in Organic Chemistry; ed. by E Schaumann, Georg Thieme Verlag: Stuttgart, Germany (1992), E8a, pp. 45–204

  100. B. Frolund, A.T. Jorgensen, L. Tagmose, T.B. Stensbol, H.T. Vestergaad, C. Engblom, U. Kristiansen, C. Sanchez, P. Krogsgaard-Larsen, T. Liljefors, J. Med. Chem. 45, 2454 (2002)

    Article  CAS  Google Scholar 

  101. W.S. Hamama, M.E. Ibrahim, H.H. Zooro, Synth. Commun. 43, 2393 (2013)

    Article  CAS  Google Scholar 

  102. A. Babulreddy, R.V. Hymavathi, M.M. Hussain, G.N. Swamy, J. Heterocycl. Chem. 50, 727 (2013)

    Article  CAS  Google Scholar 

  103. M. Brahmayya, B. Venkateswararao, D. Krishnarao, S. Durgarao, U.V. Prasad, T. Damodharam, R. Mishra, J. Pharm. Res. 7, 516 (2013)

    CAS  Google Scholar 

  104. H. Song, W.B. Feng, F. Cheng, D.Q. Shi, J. Heterocycl. Chem. 47, 1310 (2010)

    Article  CAS  Google Scholar 

  105. J.P. Demers, W.E. Hageman, S.G. Johnson, D.H. Klaubert, R.A. Look, J.B. Moore, Bioorg. Med. Chem. Lett. 4, 2451 (1994)

    Article  CAS  Google Scholar 

  106. W.M. Abdou, R.F. Barghash, R.E. Khidre, Monatsh. Chem. 144, 1233 (2013)

    Article  CAS  Google Scholar 

  107. C. Changtam, P. Hongmanee, A. Suksamrarn, Eur. J. Med. Chem. 45, 4446 (2010)

    Article  CAS  Google Scholar 

  108. S.K. Laughlin, M.P. Clark, J.F. Djung, A. Golebiowski, T.A. Brugel, M. Sabat, R.G. Bookland, M.J. Laufersweiler, J.C. VanRens, J.A. Townes, B. De, L.C. Hsieh, S.C. Xu, R.L. Walter, M.J. Mekel, M.J. Janusz, Bioorg. Med. Chem. Lett. 15, 2399 (2005)

    Article  CAS  Google Scholar 

  109. V.K. Sharma, S.K. Mishra, N. Nesnas, Environ. Sci. Technol. 40, 7222 (2006)

    Article  CAS  Google Scholar 

  110. S.A. Lawrence, V. Roth, R. Slinger, B. Toye, I. Gaboury, B. Lemyre, BMC Pediatr. 5, 49 (2005)

    Article  Google Scholar 

  111. D.V. Vorobyeva, N.M. Karimova, I.L. Odinets, G.V. Roschenthaler, S.N. Osipov, Org. Biomol. Chem. 9, 7335 (2011)

    Article  CAS  Google Scholar 

  112. T. Ishioka, A. Kubo, Y. Koiso, K. Nagasawa, A. Itaib, Y. Hashimotol, Bioorg. Med. Chem. 10, 1555 (2002)

    Article  CAS  Google Scholar 

  113. T. Ishioka, A. Tanatani, K. Nagasawa, Y. Hashimoto, Bioorg. Med. Chem. Lett. 13, 2655 (2003)

    Article  CAS  Google Scholar 

  114. Q. Liu, Y.N. Zhang, Bull. Korean Chem. Soc. 32, 3559 (2011)

    Article  CAS  Google Scholar 

  115. Q. Liu, X. Hou, Phosphorus, Sulfur Silicon Relat. Elem. 187, 448 (2012)

    Article  CAS  Google Scholar 

  116. Q. Liu, R.T. Wu, J. Chem. Res. 35, 598 (2011)

  117. M. Mirzadeh, G.H. Mahdavinia, EJ Chem. 9, 425 (2012)

    Article  Google Scholar 

  118. F. Saikh, J. Das, S. Ghosh, Terahedron Lett. 54, 4679 (2013)

    Article  CAS  Google Scholar 

  119. K. Ablajan, H. Xiamuxi, Synth. Commun. 42, 1128 (2012)

    Article  CAS  Google Scholar 

  120. Q.F. Cheng, X.Y. Liu, Q.F. Wang, L.S. Liu, W.J. Liu, Q. Lin, X.J. Yang, Chin. J. Org. Chem. 29, 1267 (2009)

    CAS  Google Scholar 

  121. K. Ablajan, H. Xiamuxi, Chin. Chem. Lett. 22, 151 (2011)

    Article  CAS  Google Scholar 

  122. Y.-Q. Zhang, J.-J. Ma, C. Wang, J.-C. Li, D.-N. Zhang, X.-H. Zang, J. Li, Chin. J. Org. Chem. 28, 141 (2008)

    Google Scholar 

  123. S. Fozooni, N.G. Hosseinzadeh, H. Hamidian, M.R. Akhgar, J. Braz. Chem. Soc. 24, 1649 (2013)

    CAS  Google Scholar 

  124. Y.Q. Zhang, C. Wang, M.Y. Zhang, P.L. Cui, Y.M. Li, X. Zhou, J.C. Li, Chin. J. Org. Chem. 28, 914 (2008)

    CAS  Google Scholar 

  125. H. Kiyani, Org. Chem. Indian J. 13, 97 (2013)

    Google Scholar 

  126. H. Kiyani, F. Ghorbani, Heterocycl. Lett. 2, 145 (2013)

    Google Scholar 

  127. H. Kiyani, F. Ghorbani, Heterocycl. Lett. 3, 359 (2013)

    CAS  Google Scholar 

  128. H. Kiyani, F. Ghorbani, Open. J. Org. Chem. 1, 5 (2013)

    Google Scholar 

  129. H. Kiyani, F. Ghorbani, Elixir Org. Chem. 58A, 14948 (2013)

    Google Scholar 

  130. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. (2013). doi: 10.1007/s11164-013-1411-x

  131. H. Kiyani, F. Ghorbani, J. Saudi Chem. Soc. (2013). doi:10.1016/j.jscs.2013.11.002

  132. E. Knoevenagel, Ber. Dtsch. Chem. Ges. 29, 172 (1896)

    Article  CAS  Google Scholar 

  133. A. Song, X. Wang, K.S. Lam, Tetrahedron Lett. 44, 1755 (2003)

    Article  CAS  Google Scholar 

  134. I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 7727 (2004)

    Article  CAS  Google Scholar 

  135. L.F. Tietze, Pure Appl. Chem. 76, 1967 (2004)

    Article  CAS  Google Scholar 

  136. Y. Zhang, Q. Dou, L. Dai, X. Wang, Y. Chen, RSC Adv. 2, 8979 (2012)

    Article  CAS  Google Scholar 

  137. S.M. Lai, R. Martin-Aranda, K.L. Yeung, Chem. Commun. 218−219 (2003). doi:10.1039/B209297B

  138. A. Yassin, T. Rousseau, P. Leriche, A. Cravino, J. Roncali, Sol. Energy Mater. Sol. Cells 95, 462 (2011)

    Article  CAS  Google Scholar 

  139. Y.D. Lin, T.J. Chow, J. Photochem, Photobiol. A: Chem. 230, 47 (2012)

    Article  CAS  Google Scholar 

  140. P. Leelavathi, S.R. Kumar, J. Mol. Catal. A: Chem. 240, 99 (2004)

    Google Scholar 

  141. T.I. Reddy, R.S. Varma, Tetrahedron Lett. 38, 1721 (1997)

    Article  CAS  Google Scholar 

  142. G. Li, J. Xiao, W. Zhang, Green Chem. 13, 1828 (2011)

    Article  CAS  Google Scholar 

  143. J. Luo, T. Xin, Y. Wang, New J. Chem. 37, 269 (2013)

    Article  CAS  Google Scholar 

  144. S. Liu, Y. Ni, J. Yang, H. Hu, A. Ying, S. Xu, Chin. J. Chem. 32, 343 (2014)

    Article  CAS  Google Scholar 

  145. H. Valizadeh, H. Gholipour, Synth. Commun. 40, 1477 (2010)

    Article  CAS  Google Scholar 

  146. S. Zhao, X. Wang, L. Zhang, RSC Adv. 3, 11691 (2013)

    Article  CAS  Google Scholar 

  147. J.M. Khurana, K. Vij, Catal. Lett. 138, 104 (2010)

    Article  CAS  Google Scholar 

  148. B.V. Kumar, H.S. Bhojyan Naik, D. Girija, B.V.J. Kumar, Chem. Sci. 123, 615 (2011)

    Article  CAS  Google Scholar 

  149. Y. Goa, P. Wu, T. Tatsumi, J. Catal. 224, 107 (2004)

    Article  CAS  Google Scholar 

  150. H. Kiyani, F. Ghorbani, Org. Chem. Indian J. 9, 367 (2013)

    CAS  Google Scholar 

  151. S. Ghosh, J. Das, S. Chattopadhyay, Tetrahedron Lett. 52, 2869 (2011)

    Article  CAS  Google Scholar 

  152. J. Han, Y. Xu, Y. Su, X. She, X. Pan, Catal. Commun. 9, 2077 (2008)

    Article  CAS  Google Scholar 

  153. Y.Q. Yu, Z.L. Wang, J. Chin. Chem. Soc. 60, 288 (2013)

    Article  CAS  Google Scholar 

  154. M.C. Pirrung, Chem. Eur. J. 12, 1312 (2006)

    Article  CAS  Google Scholar 

  155. S. Chitra, N. Paul, S. Muthusubramanian, P. Manisankar, Green Chem. 13, 2777 (2011)

    Article  CAS  Google Scholar 

  156. Organic Reactions in Water: Principles, Strategies and Applications, ed. by U.M. Lindström (Blackwell, Oxford, 2007)

  157. D.P. Debecker, E.M. Gaigneaux, G. Busca, Chem. Eur. J. 5, 3920 (2009)

    Article  CAS  Google Scholar 

  158. K. Tanabe, W.F. Holderich, Appl. Catal. A 181, 399 (1999)

    Article  CAS  Google Scholar 

  159. L. McMills, F. Nyasulu, R. Barlag, J. Chem. Educ. 89, 958 (2012)

    Article  CAS  Google Scholar 

  160. D.R. White, N.A. Harris, J.P. Rife, J. Chem. Eng. Data 34, 347 (1989)

    Article  CAS  Google Scholar 

  161. J. Li, H.D.H. Stöver, Langmuir 24, 13237 (2008)

    Article  CAS  Google Scholar 

  162. S. Parthiban, S. Murali, G. Madhurambal, S.P. Meenakshisundaram, S.C. Mojumdar, J. Therm. Anal. Calorim. 100, 751 (2010)

    Article  CAS  Google Scholar 

  163. K. Muthu, G. Bhagavannarayana, C. Chandrasekaran, S. Parthiban, S.P. Meenakshisundaram, S.C. Mojumdar, J. Therm. Anal. Calorim. 100, 793 (2010)

    Article  CAS  Google Scholar 

  164. H. Kiyani, F. Ghorbani, Chem. Pap. 68, 1104 (2014)

    Article  CAS  Google Scholar 

  165. H. Kiyani, F. Ghorbani, J. Saudi Chem. Soc. 18, 689 (2014)

    Article  CAS  Google Scholar 

  166. H. Kiyani, F. Ghorbani, Res. Chem. Intermed. (2013). doi: 10.1007/s11164-013-1508-2

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The authors are grateful to the Damghan University.

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  1. School of Chemistry, Damghan University, 36715-364, Damghan, Iran

    Hamzeh Kiyani & Fatemeh Ghorbani

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  1. Hamzeh Kiyani
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  2. Fatemeh Ghorbani
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Correspondence to Hamzeh Kiyani.

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Kiyani, H., Ghorbani, F. Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water. Res Chem Intermed 41, 7847–7882 (2015). https://doi.org/10.1007/s11164-014-1863-7

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