Document Type : Short communication

Authors

1 Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran

2 Department of Chemistry, Payame Noor University, PO Box 19395‐3697 Tehran, Iran

Abstract

In this study, acidic ionic liquid N, N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} was utilized to promote two classes of useful organic transformations under solvent-free conditions including, i) the condensation of arylaldehydes with malononitrile and 1-naphthol, leading to 2-amino-4H-chromenes, and ii) the condensation reaction of arylaldehydes with 2-naphthol to give 14-aryl-14H-dibenzo[a, j]xanthenes. The ionic liquid efficiently catalyzed the reactions, and the products were obtained in excellent yields (94-98%) within short reaction times (8-30 min).

Graphical Abstract

Efficient production of 2-amino-4H-chromenes and 14-aryl-14H-dibenzo[a, j]xanthenes catalyzed by N, N-diethyl-N-sulfoethanaminium hydrogen sulfate

Keywords

Main Subjects

[1]. Hasaninejad A., Zare A., Shekouhy M., Ameri Rad J.J. Comb. Chem., 2010, 12:844

[2]. Zolfigol M.A., Khazaei A., Moosavi-Zare A.R., Zare A., Kruger H.G., Asgari Z., Khakyzadeh V., Kazem-Rostami M. J. Org. Chem., 2012, 77:3640

[3]. Hajipour A.R., Rafiee F. Org Prep Proced Int.,  2015, 47:249

[4]. Ghaffari Khaligh N., Mihankhah T., Johan M.R. J Mol Liq., 2019, 277:794

[5]. Han X-X., Du H., Hung C-T., Liu L-L., Wu P-H., Ren D-H., Huang S-J., Liu S-B. Green Chem., 2015, 17:499

[6]. Al Otaibi A., Deane F.M., Russell C.C., Hizartzidis L., McCluskey S.N., Sakoff J.A., McCluskey A. RSC Adv., 2019, 9:7652

[7]. Karami M., Maghsoudi M., Merajoddin M., Zare A. Asian J Nanosci Mater, 2019, 2:413

[8]. Rezayati S., Hajinasiri R., Hossaini Z., Abbaspour S. Asian J Green Chem., 2018, 2:268

[9]. Zare A., Nasouri Z.  J Mol Liq., 2016,  216:364

[10]. Sajjadifar S., Mohammadi-Aghdam S. Asian J Green Chem., 2017, 1:1

[11]. Karami M., Gholami B., Hekmat Zadeh T., Zare A. Chem Methodol., 2019, 3:509

[12]. Irannejad-Gheshlaghchaei N., Zare A., Sajadikhah S.S., Banaei A. Res Chem Intermed., 2018, 44:6253

[13]. Patel A.S., Tala S.D., Nariya P.B., Ladva K.D., Kapuriya N.P. J Chin Chem Soc., 2019, 66:247

[14]. Kumar D., Reddy V.B., Mishra B.G., Rana R.K., Nadagouda M.N., Varma R.S. Tetrahedron., 2007, 63:3093

[15]. Rostami A., Atashkar B., Gholami H. Catal Commun., 2013, 37:69

[16]. Dekamin M.G., Eslami M., Maleki A. Tetrahedron., 2013, 69:1074

[17]. Baghernejad B., Heravi M.M., Oskooie H.A. J Korean Chem Soc., 2009, 53:631

[18]. Pourhasan B., Mohammadi‐Nejad A. J Chin Chem Soc., 2019, 66:1356

[19]. Safari J., Javadian L. Ultrason Sonochem., 2015, 22:341

[20]. Jin T-S., Xiao J-C., Wang S-J., Li T-S. Ultrason Sonochem., 2004, 11:393

[21]. Khafagy M.M., El-Wahas A.H.F.A., Eid F.A., El-Agrody A.M. Il Farmaco., 2002, 57:715

[22]. Mohr S.J., Chirigos M.A., Fuhrman F.S., Pryor J.W. Cancer Res., 1975, 35:3750

[23]. Martinez A.G., Marco L.J. Bioorg Med Chem Lett., 1997, 7:3165

[24]. Bianchi G., Tava A. Agric Biol Chem., 1987, 51:2001

[25]. Hafez E.A., Elnagdi M.H., Elagamey A.A., El-Taweel F.A.M. Heterocycles., 1987, 26:903

[26]. Ellis G.P. The Chemistry of Heterocyclic Compounds. Chromenes, Harmones, and Chromones. Weissberger A, Taylor EC (Eds.); John: New York, NY; Chapter II., 1977, pp 11

[27]. Naeimi H., Nazifi Z.S. Appl Catal A: Gen., 2014, 477:132

[28]. Harichandran G., Amalraj S.D., Shanmugam P. J Mol Catal A: Chem., 2014, 392:31

[29]. Mouradzadegun A., Mostafavi M.A., Ganjali M.R. J Incl Phenom Macrocycl Chem., 2018, 91:25

[30]. Mirjalili B.F., Bamoniri A., Akbari A., Taghavinia N. J Iran Chem Soc., 2011, 8:S129

[31]. Shirini F., Abedini M., Pourhasan R. Dyes Pigm., 2013, 99:250

[32]. Dashtizadeh M., Khalili M., Reghbat F., Abdi E., Bahadori Z., Sadripour Z., Zare A., Didehban K., Sajadikhah S.S. Iran Chem Commun., 2019, 7:257

[33]. Zare A., Merajoddin M., Abi F., Moosavi-Zare A.R., Mokhlesi M., Zolfigol M.A., Asgari Z., Khakyzadeh V., Hasaninejad A., Khalafi-Nezhad A., Parhami A. J Chin Chem Soc., 2012, 59:860

[34]. Ghaffari Khaligh N., Shirini F. Ultrason Sonochem., 2015, 22:397

[35]. Zolfigol M.A., Moosavi-Zare A.R., Arghavani-Hadi P., Zare A., Khakyzadeh V., Darvishi G. RSC Adv., 2012, 2:3618

[36]. Qiao Y.F., Okazaki T., Ando T., Mizoue K., Kondo K., Eguchi T., Kakinuma K. J Antibiot., 1998, 51:282

[37]. Song Y.B., Yang Y.H., You J., Liu B., Wu L.J., Hou Y.L., Wang W.J., Zhu J.X. Chem Pharm Bull., 2013, 61:167

[38]. Poupelin J.P., Ruf G.S., Blanpin O.F., Narcisse G., Ernouf G.U., Lacroix R. Eur J Med Chem., 1978, 13:67

[39]. Knight C.G., Stephens T. Biochem J., 1989, 258:683

[40]. De S., Das S., Girigoswami A. Spectrochim Acta A: Mol Biomol Spectr., 2005, 61:1821