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One-pot synthesis of some 2-amino-4H-chromene derivatives using triethanolamine as a novel reusable organocatalyst under solvent-free conditions and its application in electrosynthesis of silver nanoparticles

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Abstract

A wide variety of 2-amino-4H-chromene derivatives with diverse substituents on the 4H-chromene ring were efficiently prepared via one-pot three-component reaction of an aromatic aldehyde and malononitrile with 2-hydroxynaphthalene-1,4-dione, ethyl acetoacetate, or naphthols in the presence of triethanolamine as a new organocatalyst under solvent-free conditions. The procedure is transition metal-free and environmentally friendly approach to various 2-amino-4H-chromene derivatives. Its advantages include short reaction time, high yields, low cost, and straightforward work-up. Triethanolamine is an efficient reusable catalyst. 2-Amino-4H-benzo[g]chromenes (ABgC) were applied as novel components of electro synthesis of silver nanoparticles.

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References

  1. Veisi, H., Maleki, B., Hamelian, M., and Sedigh Ashrafi, S., RSC Adv., 2015, vol. 5, no. 9, p. 6365

    Article  CAS  Google Scholar 

  2. Maleki, B., Org. Prep. Proced. Int., 2015, vol. 47, no. 2, p. 173178

    Google Scholar 

  3. Maleki, B., and Taimazi, F., Org. Prep. Proced. Int., 2014, vol. 46, no. 3, p. 252

    Article  CAS  Google Scholar 

  4. Maleki, B., Rezaei-Seresht, E., and Ebrahimi, Z., Org. Prep. Proced. Int., 2015, vol. 47, no. 2, p. 149.

    Article  CAS  Google Scholar 

  5. Hatakeyama, S., Ochi, N., Numata, H., and Takano, S., J. Chem. Soc. Chem. Commun., 1988, vol. 17, p. 1202

    Article  Google Scholar 

  6. Singh, K., Singh, J., and Singh, H., Tetrahedron, 1996, vol. 52, no. 45, p. 14273

    Article  CAS  Google Scholar 

  7. Martín, N., Martínez-Grau, A., Seoane, C., Marco, J.L., Albert, A., and Cano, F.H., Lieb. Ann. Chem., 1993, vol. 7, no. 7, p. 801.

    Article  Google Scholar 

  8. Kidwai, M., Saxena, S., Rahman-Khan, M.K., and Thukral, S.S., Bioorg. Med. Chem. Lett., 2005, vol. 15, no. 19, p. 4295.

    Article  CAS  Google Scholar 

  9. Pospisil, J. and Marko, I. E., J. Am. Chem. Soc., 2007, vol. 129, no. 12, p. 3516. doi 10.1021/ja0691728

    Article  CAS  Google Scholar 

  10. El-Saghier, A.M., Naili., M.B., Rammash, B.K., Saleh, N.A., and Kreddan, K.M., Arkivoc, 2007, vol. 16, p. 83.

    Google Scholar 

  11. Suresh, T., Arunima, V., Atin, K., Sandeep, G., Prarthana, V.R., and Ganesh, R.K., Acta. Pol. Pharm., 2010, vol. 67, p. 423.

    Google Scholar 

  12. Jain, N., Xu, J., Kanojia, R.M., Du, F., Jian, Z.G., Emmanuel, P., and Sui, Z., J. Med. Chem., 2009, vol. 52, no. 23, p. 7544. doi 10.1021/jm900146e

    Article  CAS  Google Scholar 

  13. Mun, J., Jabbar, A.A., Devi, N.S., Liu, Y., Van-Meir, E.G., and Goodman, M.M., Bioorg. Med. Chem., 2012, vol. 20, no. 14, p. 4590. doi 10.1016/j.bmc.2012.04.064

    Article  CAS  Google Scholar 

  14. Banskota, A.H., Tezuka, Y., Tran, K.Q., Saiki, I., Miwa, Y., Taga, T., and Kadota, S., Bioorg. Med. Chem. Lett., 1998, vol. 8, no. 24, p. 3519. doi 10.1016/S0960-894X(98)00644-1

    Article  CAS  Google Scholar 

  15. Cheng, J. F., Ishikawa, A., Ono, Y., Arrhenius, T., and Nadzan, A., Bioorg. Med. Chem. Lett., 2003, vol. 13, no. 21, p. 3647. doi 10.1016/j.bmcl.2003.08.025

    Article  CAS  Google Scholar 

  16. Denish, C K., Hetal, K.P., and Nilesh, K.G., Asian. J. Biochem. Pharm. Res., 2012, vol. 2, p. 126.

    Google Scholar 

  17. Changsheng, Y., Chenxia, Y., Tuanjie, L., and Shujiang, T., Chin. J. Chem., 2009, vol. 27, no. 10, p. 1989. doi 10.1002/cjoc.200990334

    Article  Google Scholar 

  18. Wang, X.H., Zhang, X.H., Tu, S.J., Shi, F., Zou, X., Yan, S., Han, Z.G., Hao, W.J., Cao, X.D., and Wu, S.S., J. Heterocycl. Chem., 2009, vol. 46, no. 5, p. 832. doi 10.1002/jhet.153

    Article  CAS  Google Scholar 

  19. Shaabani, A., Ghadari, R., Ghasemi, S., Pedarpour, M., Rezayan, A.H., Sarvary, A., and Ng, S.W. J., Comb. Chem., 2009, vol. 11, no. 6, p. 956. doi 10.1021/cc900101w

    Article  CAS  Google Scholar 

  20. Magedov, I.V., Kireev, A.S., Jenkins, A.R., Evdokimov, N.M., Lima, D.T., Tongwa, P., Altig, J., Steelant, W.F.A., Slambrouck, S.V., Antipin, M.Y., and Kornienko, A., Bioorg. Med. Chem. Lett., 2012, vol. 22, no. 16, p. 5195. doi 10.1016/j.bmcl.2012.06.073

    Article  CAS  Google Scholar 

  21. Khurana, J.M., Nand, B., and Saluja, P., Tetrahedron, 2010, vol. 66, no. 30, p. 5637. doi 10.1016/j.tet.2010.05.082

    Article  CAS  Google Scholar 

  22. Shaterian, H.R. and Mohammadnia, M., J. Mol. Liq., 2013, vol. 177, p. 353. doi 10.1016/j.molliq.2012.10.012

    Article  CAS  Google Scholar 

  23. Yu, Y., Guo, H., and Li, X., J. Heterocycl. Chem., 2011, vol. 48, no. 6, p. 1264. doi 10.1002/jhet.747

    Article  CAS  Google Scholar 

  24. Khorami, F. and Shaterian, H.R., Res. Chem. Intermed., 2015, vol. 41, no. 5, p. 3171. doi:10.1007/s11164-013-1423-6

    Article  CAS  Google Scholar 

  25. Shaterian, H.R. and Kangani, M., Sci. Iran., 2013, vol. 20, no. 3, p. 571. doi 10.1016/j.scient.2012.11.019

    CAS  Google Scholar 

  26. Maleki, B., Babaee, S., and Tayebee, R., Appl. Organomet. Chem., 2015, vol. 29, no. 29, p. 408. doi 10.1002/aoc.3306

    Article  CAS  Google Scholar 

  27. Brahmachari, G. and Banerjee, B., ACS Sustain. Chem. Eng., 2014, vol. 2, no. 3, p. 411. doi 10.1021/sc400312n

    Article  CAS  Google Scholar 

  28. Khan, A.T., Lal, M., Ali, S., and Khan, M.M., Tetrahedron Lett., 2011, vol. 52, no. 41, p. 5327. doi 10.1016/j.tetlet.2011.08.019

    Article  CAS  Google Scholar 

  29. Kumar, D., Reddy, V.B., Sharad, S., Dube, U., and Kapur, S., Eur. J. Med. Chem., 2009, vol. 44, no. 9, p. 3805. doi 10.1016/j.ejmech.2009.04.017

    Article  CAS  Google Scholar 

  30. Moshtaghi Zonouz, A., Moghani, D., and Okhravi, S., Current. Chem. Lett., 2014, vol. 3, no. 2, p. 71.

    Article  Google Scholar 

  31. Moshtaghi Zonouz, A., Eskandari, I., and Moghani, D., Chem. Sci. Trans., 2012, vol. 1, no. 1, p. 91. doi 10.7598/cst2012.143

    Article  Google Scholar 

  32. Sánchez, A., Hernández, F., Cruz, P.C., Alcaraz, Y., Tamariz, J., Delgado F., and Vázquez, M.A., J. Mex. Chem. Soc., 2012, vol. 56, no. 2, p. 121.

    Google Scholar 

  33. Bihani, M., Bora, P.P., and Bez, G., J. Chem., 2013, p. 785930. doi 10.1155/2013/785930

    Google Scholar 

  34. Heravi, M.M., Beheshtiha, Y.S., Pirnia, Z., Sadjadi, S., and Adibi, M., Synth. Comm., 2009, vol. 39, no. 20, p. 3663. doi 10.1080/00397910902796102

    Article  CAS  Google Scholar 

  35. Heravi, M.M., Zakeri, M., and Mohammadi, N., Chin. J. Chem., 2011, vol. 29, no. 6, p. 1163. 10.1002/cjoc.201190217

    Article  CAS  Google Scholar 

  36. Babu, N.S., Pasha, N., Rao, K.V., Prasad, P.S., and Lingaiah, N., Tetrahedron. Lett., 2008, vol. 49, no. 17, p. 2730. doi 10.1016/j.tetlet.2008.02.154

    Article  CAS  Google Scholar 

  37. Wang, X.S., Zhou, J. X., Zeng, Z.S., Li, Y.L., Shi, D.Q., and Tu, S., Arkivoc, 2006, vol. 11, p. 107.

    Google Scholar 

  38. Rathod, S., Arbad, B., and Land, M., Chin. J. Catal., 2010, vol. 31, no. 6, p. 631. doi 10.1016/S1872-2067 (09)60078-4

    Article  CAS  Google Scholar 

  39. Li, Y., Chen, H., Shi, C., and Ji, S., J. Comb. Chem., 2010, vol. 12, no. 2, p. 231. doi 10.1021/cc9001185

    Article  CAS  Google Scholar 

  40. Heravi, M.M., Baghernejad, B., and Oskooie, H.A., J. Chin. Chem. Soc., 2008, vol. 55, no. 3, p. 659. doi 10.1002/jccs.200800098

    Article  CAS  Google Scholar 

  41. Mosaddegh, E. and Hassankhani, A., Ultrason. Sonochem., 2013, vol. 20, no. 6, p. 1436. doi 10.1016/j.ultsonch.2013.04.008

    Article  CAS  Google Scholar 

  42. Jin, T.S., Xiao, J.C., Wang, S.J., and Li, T.S., Ultrason. Sonochem., 2004, vol. 11, no. 6, p. 393. doi 10.1016/j.ultsonch.2003.10.002

    CAS  Google Scholar 

  43. Behbahani, F.K. and Sadeghi, M., J. Korean. Chem. Soc., 2013, vol. 57, no. 3, p. 357. doi 10.5012/jkcs.2013.57.3.357

    Article  CAS  Google Scholar 

  44. Dekamin, M.G., Eslami, M., and Maleki, A., Tetrahedron, 2013, vol. 69, no. 3, p. 1074. doi 10.1016/j.tet.2012.11.068

    Article  CAS  Google Scholar 

  45. Maleki, B. and Sheikh, S., RSC Advances., 2015, vol. 5, no. 54, p. 42997. doi 10.1039/C5RA04458H

    Article  CAS  Google Scholar 

  46. Sabitha, G., Bhikshapathi, M., Nayak, S., Srinivas, R., and Yadav, J.S., J. Heterocycl. Chem., 2011, vol. 48, no. 2, p. 267. doi 10.1002/jhet.544

    Article  CAS  Google Scholar 

  47. Maleki, B. and Sheikh, S., Org. Prep. Proced. Int., 2015, vol. 47, no. 5, p. 368. doi 10.1080/00304948.2015.1066647

    Article  CAS  Google Scholar 

  48. Baghayeri, M., Nazarzadeh Zare, E., and Namadchian, M., Sensor Actuat. B-Chem., 2013, vol. 182, p. 467. doi 10.1016/j.snb.2013.07.028

    Article  Google Scholar 

  49. Baghayeri, M., Nazarzadeh Zare, E., and Mansour Lakouraj, M., Acta., 2015, vol. 182, nos. 3–4, p. 771. doi 10.1007/s00604-014-1387-2

    CAS  Google Scholar 

  50. Baghayeri, M., Nazarzadeh Zare, E., and Mansour Lakouraj, M., Sensor. Actuat. B: Chem., 2014, vol. 202, p. 1200. doi 10.1016/j.snb.2014.06.019

    Article  CAS  Google Scholar 

  51. Baghayeri, M., Nazarzadeh Zare, E., and Mansour Lakouraj, M., Biosens. Bioelectron., 2014, vol. 55, p. 259. doi 10.1016/j.bios.2013.12.033

    Article  CAS  Google Scholar 

  52. Ameen, S., Akhtar, M.S., Umar, A., and Shin, H.S., Chem. Eng. J., 2013, vol. 229, p. 267. doi 10.1016/j.cej.2013.05.112

    Article  CAS  Google Scholar 

  53. Li, J. and Lee, E.C., Biosens. Bioelectron., 2015, vol. 71, p. 414. doi 10.1016/j.bios.2015.04.045

    Article  CAS  Google Scholar 

  54. Salimi, A., Kurd, M., Teymourian, H., and Hallaj, R., Sensor. Actuat. B: Chem., 2014, vol. 205, p. 136. doi 10.1016/j.snb.2014.08.035

    Article  CAS  Google Scholar 

  55. Khoraamabadi-Zad, A., Azadmanesh, M., Karamian, R., Asadbegy, M., and Akbari, M., RSC Adv., 2014, vol. 4, p. 47721

    Article  CAS  Google Scholar 

  56. Li, H.J. and Wang, L., Eur. J. Org. Chem., 2006, vol. 22, p. 5099.

    Article  Google Scholar 

  57. Sohoni, S., Sridhar, R., and Mandal, G., Powder. Technol., 1991, vol. 67, p. 277.

    Article  CAS  Google Scholar 

  58. Kirillov, A.M., Kopylovich, M.N., Kirillova, M.V., Haukka, M., da-Silva, M.F., and Pombeiro, A., J. Angew. Chem. Int. Ed., 2005, vol. 44, p. 4345.

    Article  CAS  Google Scholar 

  59. Pati, R.K., Ray, J.C., and Pramanik, P., J. Am. Ceram. Soc., 2001, vol. 84, p. 2849

    Article  CAS  Google Scholar 

  60. Liu, Y.Q. and Gao, L., J. Am. Ceram. Soc., 2003, vol. 86, p. 1651.

    Article  CAS  Google Scholar 

  61. Xiao, B., Sun, J., Wang, J., Liu, C., and Cheng, W., Synth. Commun., 2013, vol. 43, p. 2985.

    Article  CAS  Google Scholar 

  62. Maleki, B., Hemmati, S., Sedrpoushan, A., and Sedigh Ashrafi, S., RSC Adv., 2014, vol. 4, p. 40505

    Article  CAS  Google Scholar 

  63. Maleki, B., and Sedigh Ashrafi, S., RSC Adv., 2014, vol. 4, p. 42873

    Article  CAS  Google Scholar 

  64. Maleki, B., Sedigh Ashrafi, S., and Tayebee, R., RSC Adv., 2014, vol. 4, p. 41521

    Article  CAS  Google Scholar 

  65. Tayebee, R., Jarrahi, M., Maleki, B., Kargar Razi, M., Mokhtari, Z.B., and Baghbanian, S.M., RSC Adv., 2015, vol. 5, p. 10869

    Article  CAS  Google Scholar 

  66. Tayebee, R., Jomei, M., Maleki, B., Kargar Razi, M., Veisi, H., and Bakherad, M., J. Mol. Liq., 2015, vol. 206, p. 119

    Article  CAS  Google Scholar 

  67. Maleki, B., Barat Nam Chalaki, S., Sedigh Ashrafi, S., Rezaee Seresht, E., Moeinpour, F., Khojastehnezhad, A., and Tayebee. R., Appl. Organomet. Chem., 2015, vol. 4, p. 290

    Article  Google Scholar 

  68. Maleki, B., Akbarzadeh, E., and Babaee, S., Dyes. Pigm., 2015, vol. 123, p. 222

    Article  CAS  Google Scholar 

  69. Maleki, B., Eshghi, H., Khojastehnezhad, A., Tayebee, R., Sedigh Ashrafi, S., Esmailian Kahoo, G., and Moeinpour, F., RSC Adv., 2015, vol. 5, p. 64850

    Article  CAS  Google Scholar 

  70. Veisi, H., Naeimi, A.R., Maleki, B., Sedigh Ashrafi, S., and Sedrpoushan, A.R., Org. Prep. Proced. Int., 2015, vol. 47, p. 309

    Article  CAS  Google Scholar 

  71. Maleki, B., Eshghi, H., Barghamadi, M., Nasiri, N., Khojastehnezhad, A., Sedigh Ashrafi, S., and Pourshiani O., Res. Chem. Int., 2016, vol. 42, p. 3071, doi 10.1007/s11164-015-2198-8

    Article  CAS  Google Scholar 

  72. Maleki, B., Mohammadi Zonoz, F., and Akhlaghi, H.A., Org. Prep. Proced. Int., 2015, vol. 47, no. 5, p. 361. doi 10.1080/00304948.2015.1066646

    Article  CAS  Google Scholar 

  73. Maleki, B., Esmailian Kahoo, G., and Tayebee, R., Org. Prep. Proced. Int., 2015, vol. 47, no. 6, p. 461. doi 10.1080/00304948.2015.1088757

    Article  CAS  Google Scholar 

  74. Maleki, B., Raei, M., Akbarzadeh, E., Ghasemnejad-Bosra, H., Sedrpoushan, A.R., Sedigh Ashrafi, S., and Nabi Dehdashti, M., Org. Prep. Proced. Int., 2016, vol. 48, no. 1, p. 62. doi 10.1080/00304948.2016.1127102

    Article  CAS  Google Scholar 

  75. Maleki, B., Org. Prep. Proced. Int., 2016, vol. 48, no. 1, p. 81. doi 10.1080/00304948.2016.1127104

    Article  CAS  Google Scholar 

  76. Maleki, B., Sheikh, E., Rezaei Seresht, E., Eshghi, H., Sedigh Ashrafi, S., Khojastehnezhad, A., and Veisi, H., Org. Prep. Proced. Int., 2016, vol. 48, no. 1, p. 37. doi 10.1080/00304948.2016.1127098

    Article  CAS  Google Scholar 

  77. Maleki, B., Davoodi, A., Vakili Azghandi, M., Baghayeri, M., Akbarzadeh, E., Veisi, H., Sedigh Ashrafi, S., and Raei, M., New J. Chem., 2016, vol. 40, no. 2, p. 1278. doi 10.1039/C5NJ02707A

    Article  CAS  Google Scholar 

  78. Baghayeri, M., Amiri, A., and Farhadi, S., Sensor. Actuat. B: Chem., 2016, vol. 225, p. 354. doi 10.1016/j.snb.2015.11.003

    Article  CAS  Google Scholar 

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Maleki, B., Baghayeri, M., Sheikh, S. et al. One-pot synthesis of some 2-amino-4H-chromene derivatives using triethanolamine as a novel reusable organocatalyst under solvent-free conditions and its application in electrosynthesis of silver nanoparticles. Russ J Gen Chem 87, 1064–1072 (2017). https://doi.org/10.1134/S1070363217050280

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