A facile one-pot ultrasound assisted synthesis of 1,8-dioxo-octahydroxanthene derivatives catalyzed by Brønsted acidic ionic liquid (BAIL) under green conditions

Hossein Naeimi; Zahra Sadat Nazifi

Journal of Industrial and Engineering Chemistry, Vol.20, No.3, 1043-1049, May, 2014

DOI10.1016/j.jiec.2013.06.041 Export Citation

A facile one-pot ultrasound assisted synthesis of 1,8-dioxo-octahydroxanthene derivatives catalyzed by Brønsted acidic ionic liquid (BAIL) under green conditions

Hossein Naeimi^†, and Zahra Sadat Nazifi

Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan 87317, Islamic Republic of Iran

E-mail:

A simple and efficient one-pot procedure for the synthesis of 1,8-dioxo-octahydroxanthene derivatives in water under ultrasound irradiation is described. These heterocycles were prepared by condensation of dimedone with various aromatic aldehydes in the presence of Brønsted acidic ionic liquids as a convenient, cheap, readily synthesized and eco-friendly catalyst. This procedure has a lot of advantages such as: excellent yields, simplicity of the workup, low cost, short reaction times and green conditions. Ionic liquids could be recycled several times without significant loss of activity and high purity.

Keywords:Ultrasonic irradiation;1,8-Dioxo-octahydroxanthene;Dimedone;Aromatic aldehydes;Ionic liquid

[References]

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[1] Li JT, Li YW, Song YL, Chen GF, Ultrason. Sonochem., 19, 1 (2012)

[2] Kowsari E, Mallakmohammadi M, Ultrason. Sonochem., 18, 447 (2011)

[3] Ghahremanzadeh R, Fereshtehnejad F, Mirzaei P, Bazgir A, Ultrason. Sonochem., 18, 415 (2011)

[4] He JY, Xin HX, Yan H, Song XQ, Zhong RG, Ultrason. Sonochem., 18, 466 (2011)

[5] Li JT, Yin Y, Sun MX, Ultrason. Sonochem., 17, 363 (2010)

[6] Pang YL, Abdullah AZ, Ultrason. Sonochem., 19, 642 (2012)

[7] Li JT, Sun MX, Yin Y, Ultrason. Sonochem., 17, 359 (2010)

[8] Bazgir A, Ahadi S, Ghahremanzadeh R, Khavasi HR, Mirzaei P, Ultrason. Sonochem., 17, 447 (2010)

[9] Shen ZL, Ji SJ, Wang SY, Zeng XF, Tetrahedron, 61, 10552 (2005)

[10] Naeimi H, Rabiei K, Bull. Chem. Soc. Jpn., 84, 1112 (2011)

[11] Hideu T, JP Tokkyo Koho (1981) 56005480 (Chem. Abstr 95 (1981) 80922b). (1981)

[12] Poupelin JP, Ruf GS, Blanpin OF, Narcisse G, Ernouf GU, Lacroix R, Eur. J. Med. Chem., 13, 67 (1978)

[13] Lambert RW, Martin JA, Merrett JH, Parkes LEB, Thomas GJ, Chem. Abstr., PCT Int. Appl. WO 9706178, 1997, 126 (1997)

[14] Ion RM, Frackowiak D, Planner A, Wiktorowicz K, Acta Biochim. Pol., 45, 833 (1998)

[15] Banerjee A, Mukherjee AK, Stain Technol., 56, 83 (1981)

[16] Ahmad M, King TA, Ko D, Cha BH, Lee J, J. Phys. D-Appl. Phys., 35, 1473 (2002)

[17] Knight CG, Stephens T, Biochem. J., 258, 683 (1989)

[18] Dadhania AN, Patel VK, Dipak K, Raval CR, Chimia, 15, 378 (2012)

[19] Venkatesan K, Pujari SS, Lahoti RJ, Srinivasan KV, Ultrason. Sonochem., 15, 548 (2008)

[20] Polshettiwar V, Decottignies A, Len C, Fihri A, Chem. Sus. Chem., 3, 502 (2010)

[21] Girijesh KV, Keshav R, RajivPratibha KVD, Singh MS, Tetrahedron, 67, 3698 (2011)

[22] Mahdavinia GH, Saeidi Hayeniaz MABY, Chin. Chem. Lett., 20, 539 (2009)

[23] Venkatesan K, Pujari SS, Lahoti RJ, Srinivasan KV, Ultrason. Sonochem., 15, 548 (2008)

[24] Swapna K, Narayana MS, Venkata DNY, Eur. J. Chem., 2, 272 (2011)

[25] Poor Heravi MR, J. Iran. Chem. Soc., 6, 483 (2009)

[26] Suslick KS, Science, 247, 1439 (1990)

[27] Mason TJ, Chem. Soc. Rev., 26, 443 (1997)

[28] Cravotto G, Cintas P, Chem. Soc. Rev., 35, 180 (2006)