Synthesis of Pyrazolopyranopyrimidine and Dihydropyrano[2,3-c]pyrazole Derivatives using Vitamin D as an Efficient Catalyst under Green Condition

Journal of Applied Chemical Research

دوره 17، شماره 1، فروردین 2023، صفحه 72-86   

نوع مقاله: Original Article

نویسندگان

Fatemeh Mir؛ Nourallah Hazeri^* ؛ Malek Taher Maghsoodlou؛ Mojtaba Lashkari

Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan, Zahedan, Iran

چکیده

An  efficient,  rapid,  and  eco-friendly  protocol  for  one-pot,  four-component  preparation  of 
dihydropyrano[2,3-c]pyrazole and pyrazolopyranopyrimidine derivatives has been developed using 
vitamin D as an efficient catalyst. This method involves several advantages such as low-cost and 
non-toxic catalysts, high yields of products, simple workup, no hazardous solvent, and no need for
column chromatography.

کلیدواژه‌ها

Dihydropyrano[2؛ 3-c]  pyrazoles؛  Pyrazolopyranopyrimidines؛  Vitamin  D؛  Green conditions

مراجع

[1]. H. Bienayme, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J.,6, 3321(2000).
[2]. T. ZarganesTzitzkas, C.G. Neochoritis, A. Domling, Acs Med. Chem. Let.,10, 389 (2019).
[3]. S. Balalaie, L. Baoosi, F. Tahoori, F. Rominger, H.R. Bijanzadeh, Tetrahedron.,69, 738 (2013).
[4]. M.N. Elinson, V.M. Merkulova, A.I. Ilovaiskya, F. Barba, B. Batanero, Electrochim. Acta., 56,
8219 (2011).

[5]. S. Verma,S.L. Jain, Terahedron Lett., 53, 6055 (2012).
[6]. I. Yavari, L. Moradi, Tetrahedron Lett.,47, 1627 (2006).
[7]. D. Azarifar, D. Sheikh, Synth. Commun.,43, 2517(2013).
[8]. A.B. Atar, J.T. Kim, K.T. Lim, Y.T. Jeong, Synth. Commun., 44, 2679 (2014).
[9]. M.A. Zolfigol, S. Baghery, A.R. MoosaviZare, S.M. Vahdat, RSC Adv., 5, 32933 (2015).
[10]. M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, A.E.Z. Rashad, Naturforsch. C.,61, 1 (2006).
[11]. S.C. Kuo, L.J. Huang, H.Nakamura, J. Med. Chem., 27, 539(1984).
[12]. N.R. Komdar, D.D. Haveliwala, P.T. Mistry, S.K. Patel, Eur. J. Med. Chem., 45, 5056 (2010).
[13]. M.C. Bagley, D.D. Hughes, M.C. Lubinu, E.A. Merrit, P.H. Taylor, N.C.O. Tomkinson, QSAR
Comb. Sci., 23, 859 (2004).
[14]. S.B. Guo, S.X. Wang, J.T. Li, Commun.,37, 2111 (2007).
[15]. J. H. Clark, Pure Appl. Chem., 73,103, (2001).
[16]. D.W.C. MacMillan, Nature., 455, 304 (2008).
[17]. P. Lips, Prog. Biophys. Mol. Biol., 92, 4, (2006).
[18]. A. Hossein-nezhad, M.F. Holick, Mayo Clin. Proc.,88, 720 (2013).
[19]. D. Bikle, J. Clin. Endocrinol. Metab., 94, 26 (2009).
[20]. A. Oudi, N. Hazeri, M. Fatahpour, J. Appl. Chem. Res., 13, 36 (2019).
[21]. M. Narouei, N. Hazeri, E. Molashahi, S. Zhaleh, M. Fatahpour, J. Appl. Chem. Res., 11, 38
(2017).
[22]. N. Hazeri, M. Lashkari, M. Fatahpour, M. Sheikhveisi, Bull. Korean. Chem. Soc.,41, 786
(2020).
[23]. M. Roozifar. N. Hazeri. H. FaroughiNiya. J. Heterocycl. Chem.,58, 1117, (2021).
[24]. B. Adrom. N. Hazeri. M. T. Maghsoodlou. M. Lashkari, M. Fatahpour, Maced. J. Chem.
Chem. Eng., 36, 223 (2017).
[25]. M. Kangani, M.T. Maghsoodlou, N. Hazeri, Chin. Chem. Lett., 27, 66, (2016).
[26]. M. Kangani, N. Hazeri, M.T Maghsoodlou,K. Khandan-Barani, M. Kheyrollahi, F.
Nezhadshahrokhabadi, J. Iran. Chem. Soc.,12, 47 (2015).
[27]. A.B. Atar, J.T. Kim, K.T. Lim, Y.T. Jeong.Synth. Commun., 44, 2679 (2014).
[28]. K. Ablajan, W. Liju, A. Tuoheti, Y. Kelimu, Lett. Org. Chem., 9, 639 (2012).
[29]. S.B. Guo, S.X. Wang, J.T. Li, Synth. Commun., 37, 2111 (2007).

[30]. A.R. MoosaviZare, M.A. Zolfigol, E. Noroozizadeh, M. Tavasoli, V. Khakyzadeh, A. Zare,
New J. Chem.,37, 4089 (2013).
[31]. W. Mingshu, F. Qinqin, W. Dehui, M. Jinya,Synth. Commun., 43, 1721 (2013).
[32]. H. FaroughiNiya, N. Hazeri, M.T. Maghsoodlou, J. Org. Chem., 11, 5472 (2020).

[33]. A.R. MoosaviZare, M.A. Zolfigol, E. Noroozizadeh, M. Tavasoli, V. Khakizadeh, A. Zare,
New J. Chem., 37, 4089(2013).
[34]. M.A. Zolfigol, M. Tavasoli, A.R. Moosavi-Zare, P. Moosavi, H.G. Kruger, M. Shiri, V.
Khakyzadeh, RSC Adv., 3, 25681(2013).
[35]. S. Dastkhoon, Z. Tavakoli, S. Khodabakhshi, New J. Chem., 39, 7268 (2015).
[36]. X.T.Li, A.D.Zhao, L.P.Mo, Z.H.Zhang, RSC Adv.,4, 51580 (2014).
[37]. M.R. Tipale, L.D. Khillare, A.R.Deshmukh, M.R. Bhosle,J.Heterocycl. Chem.,55, 716 (2018).
[38]. S. Sadjadi, M.M. Heravi, M. Daraie, Res. Chem. Intermed., 43, 2201 (2017).
[39]. S. Dastkhoon, Z. Tavakoli, S. Khodabakhshi, M. Baghernejad, M. Khaleghi
Abbasabadi, New J. Chem., 39, 7268 (2015).
[40]. S.H.S.Azzam, M.A. Pasha, Tetrahedron Lett.,53, 6834 (2012).
[41]. C.F.Zhou, J.J. Li, W.K.Su,Chin. Chem. Lett., 27, 1686 (2016).
[42]. M. Kangani, N. Hazeri, M.T. Maghsoodlou, K. KhandanBarani, M. Kheyrollahi, F.
Nezhadshahrokhabadi, J. Iran. Chem. Soc., 12, 47 (2015).
[43]. S. Khodabakhshi, A. Rashidi, Z. Tavakoli, M. Baghernejad, A. Yadegari, Monatsh. Chem.,147,
791 (2016)