CiteScore: 1.9     h-index: 21

Document Type : Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran

2 Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, Iran

Abstract

Simple and efficient protocols have been developed for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes. (i) A cost-effective, simple and convenient procedure for the synthesis of aryl-14H-dibenzo[a,j]xanthenes has been developed via a one-pot condensation from substituted benzaldehydes (1 equiv) and β-naphthol (2 equiv) in the presence of 2,6-pyridinedicarboxylic acid (2,6-PDCA) under solvent-free conditions. (ii) The one-pot condensation of substituted benzaldehydes (1 equiv) and 5,5-dimethyl-1,3-cyclohexanedione (dimedone) (2 equiv) in the presence of 2,6-pyridinedicarboxylic acid (2,6-PDCA) under solvent-free conditions leads to 1,8-dioxo-octahydro-xanthenes. In these protocols several advantages such as: Excellent yields, very short reaction times, easy work-up, simple methodology and ease of preparation and regeneration of the catalyst are offered. In these protocols several advantages such as: Excellent yields, very short reaction times, easy work-up, simple methodology and ease of preparation and regeneration of the catalyst are offered.

Graphical Abstract

2,6-Pyridinedicarboxylic acid as an efficient and mild organocatalyst for the one-pot synthesis of xanthene derivative

Keywords

Main Subjects

[1]. Lambert R.W., Martin J.A., Merrett J.H., Parkes K.E.B., Thomas G.J. PCT Int. Appl. WO9706178, 1997
[2]. Takeshiba H., Jiyoujima T. Japan Kokai Tokkyo Koho JP 56005480. Tokyo: Japan Patent Office, 1981
[3]. Poupelin J.P., Saint-Ruf G., Foussard-Blanpin O., Narcisse G., Uchida-Ernouf G., Lacroix R. Eur. J. Med. Chem, 1978, 13:67
[4]. Ahmad M., King T.A., Ko Do-K., Cha B.H., Lee J. J. Phys. D: Appl. Phys, 2002, 35:1473
[5]. Knight C.G., Stephens T. Biochem. J, 1989, 258:683
[6]. Kitahara Y., Tanaka K. Chem. Commun, 2002, 932 DOI: 10.1039/b110514k
[7]. Nagarapu L., Kantevari S., Mahankhali V.C., Apuri S. Catal. Commun, 2007, 8:1173
[8]. Pasha M.A., Jayashankara V.P. Bioorg. Med. Chem. Lett, 2007, 17:621
[9]. Bigdeli M.A., Heravi M.M., Mahdavinia G.H. J. Mol. Catal A: Chemical, 2007, 275:25
[10]. Patil S.B., Bhat R.P., Samant S.D. Synth. Commun, 2006, 36:2163
[11]. Wang J.Q., Harvey G.R. Tetrahedron, 2002, 58:5927
[12]. Knignt D.W., Little P.B. Synlett, 1998, 10:1141
[13]. Kuo C.W., Fang J.M. Synth. Commun, 2001, 31:877
[14]. Jha A., Beal J. Tetrahedron Lett, 2004, 45:8999
[15]. Dharma Rao, G.B., Kaushik M.P.,Halve A.K. Tetrahedron Lett,  2012, 53:2741
[16]. Mokhtary M., Refahati S. Dyes Pigm, 2013, 99:378
[17]. Tayebee R., Tizabi SH. Chin. J. Catal, 2012, 33:962
[18]. Nazari S., Keshavarz M., Karami B., Iravani N., Vafaee-Nezhad M. Chin. Chem. Lett, 2014, 25:317
[19]. Shirini F., Ghaffari Khaligh N. Dyes Pigm, 2012, 95:789
[20]. Sivaguru P.,  Lalitha, A. Chin. Chem. Lett, 2013, 25:3231
[21]. Zolfigol M.A., Khakyzadeh V., Moosavi-Zare A.H., Zare A., Azimi S.B., Asgari ZH. Hasaninejad A.R. C. R. Chim, 2012, 15:719
[22]. Shirini F., Yahyazadeh A., Mohammadi K. Chin. Chem. Lett, 2014, 25:341
[23]. Dabiri M., Azimi S.C., Bazgir A. Chem. Pap, 2008, 62:522
[24]. Noroozi Tisseh Z., Azimi A.C., Mirzaei P., Bazgir A. Dyes Pigm, 2008, 79:273
[25]. Khosropour A.R., Khodaei M.M., Moghannian H. Synlett, 2005, 6:955
[26]. Saini A., Kumar S., Sandhu J.S. Synlett, 2006, 2006:1928
[27]. Sajjadifar S., Rezayati S. Chem. Pap, 2014, 68:531
[28]. Kiasat A.R., Fallah-Mehrjardi M. J. Braz. Chem. Soc, 2008, 19:1595
[29]. Hajinasiri R., Rezayati S. Z. Naturforsch, 2013, 68b:818
[30]. Hajipour A.R., Khazdooz L., Ruoho A.E. Catal. Commun, 2008, 9:89
[31]. Dabiri M., Baghbanzadeh M., Shakouri Nikcheh M., Arzroomchilar E. Bioorg. Med. Chem. Lett, 2008, 18:436
[32]. Das B., Ravikanth B., Ramu R., Laxminarayana K., Vittal Rao B. J. Mol. Catal A: Chemical, 2006, 255:74
[33]. Shaterian H.R., Ghashang M., Hassankhani A. Dyes Pigm, 2008, 76:564
[34]. Kumar P.S., Kumar S., Rajitha B., Reddy N., Sreenivasulu P., Thirupathi Reddy Y. Arkivoc, 2006, xii:46
[35]. Rajitha B., Sunil Kumar B., Thirupathi Reddy Y., Nar-simha Reddy P., Sreenivasulu N. Tetrahedron Lett, 2005, 46:8691
[36]. Ko S., Yao C.F. Tetrahedron Lett, 2006, 47:8827
[37]. Das B., Ravikanth B., Ramu R., Laxminarayana K., Rao B.V. J. Mol. Catal A: Chemical, 2006a, 255:74
[38]. Seyyedhamzeh M., Mirzaei P., Bazgir A. Dyes Pigm, 2007, 76:836
[39]. Shakibaei G.I., Mirzaei P., Bazgir A. Applied Catalalysis A: General, 2007, 325:188
[40]. Kantevari S., Bantu R., Nagarapu L. Arkivoc, 2006, xvi:136