Application of N-isocyaniminotriphenyl phosphorane for preparation of heterocyclic acrylate as a key constituent of many industrial and pharmaceutical compounds

Journal of Applied Chemical Research

دوره 17، شماره 1، فروردین 2023، صفحه 87-98   

نوع مقاله: Original Article

نویسندگان

Milad Bazaz Rastkar¹؛ Bita Mohtat^{* 1}؛ Gholam Bagheri Marandi¹؛ Hoorieh Djahaniani²

¹Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran

²Department of Chemistry, East Tehran Branch, Islamic Azad University, Tehran, Iran

چکیده

2-Hydroxy  pyridine  undergoes  a  smooth  reaction  with  electron-deficient  acetylenic  esters  in  the 
presence  of  N-isocyaniminotriphenyl  phosphorane  under  reflux  conditions  to  produce  the 
heterocyclic  acrylate  compounds  in  high  yields.  The  acrylate  structures  with  E/Z  isomers  were 
obtained  when  the  reaction  was  performed  with  4-Hydroxy pyridine  and  4-Hydroxy quinazoline, 
the  acrylate  structures  with  E/Z  isomers  were obtained.  All  compounds  have many applications in 
medicinal  and  industrial  chemistry—configuration  of  E/Z  isomers  distinguished  with  nuclear 
magnetic resonance technique and chemical shift of olefinic proton. The method offers a simple and 
efficient  route  for  preparing  acrylate  heterocyclic  compared  to  the  other  methodologies.  The 
structures of the products were deduced and supported by 1HNMR and IR spectroscopy. 

کلیدواژه‌ها

N-isocyaniminotriphenylphosphorane؛ Electron-deficient acetylenic esters؛ Acrylate heterocyclic compounds؛ 4-Hydroxy pyridine؛ 4-Hydroxy quinazoline

مراجع

[1]. Ch. Xiaoyan, W. Huang, B. He, Y. Zhang, Polymers, 14, 557 (2022).
[2]. T. Avalos, A. Josue, R. Leonardo, R. Cajero-Zul, M. Vazquez-Lepe, A. Fernando, L. Dellamary,
A. Martinez-Richa, K.A. Barrera-Rivera, F.L. Serrano, S.M. Nuno-Donlucas, Polymers, 13, 533
(2021).
[3]. M. Silvija, P. Grbcic, S. Shammugam, M. Radic Stojkovic, K. Pavelic, M. Sedic, S. Kraljevic,
S. Raic-Malic, Molecules, 26, 7060 (2021).
[4]. J. Suresh, E. Vakees, S. Karthik, M. Kayalvizhi, A. Arun, Des. Monomers Polym.,17, 753
(2014).
[5]. B. Hajimohammadi, S. M. Athari, M. Abdollahi, Gh. Vahedi, S. Sh. Athari, Front.Immunol.,11,
1940 (2020).
[6]. A. Hugo, R. Katarzyna. M. Targowska-Duda, D. Feuerbach, K. Jozwiak, Neurochem. Int., 87,
110 (2015).
[7]. D. Barrios, A.G. GonzAlez, C. Reinoso, J. Santiana, F. Quiroz, J.I. Chango, C. Costa Vera, L.
Caniglia, V. Salazar, M.F. Delgado, Mater.Chem.Phys., 255, 123476 (2020).
[8]. M.I. Yakhkind, K.R. Tarantseva, M.A. Marynova, P.A. Storozhenko, M.M. Rasulov.
Russ.Chem.Bull., 63, 1056 (2014).
[9]. A. Liping, Y. Wang, Xi. Liu, M. Ning, D. Haiying, J. Minghua, L. Ying, L. Zhang, xu. Yanling,
H. peili, S. Zhiwei,Chem.Pharm. Bull.,59, 563 (2011).
[10]. P. Eleni, A. Peperidou, I. Fotopoulos, H.L. Dimitra, Curr.Pharm.Biotechnol.,19, 1048 (2018).
[11]. C. Carmelo, G. Neri, A. Santoro, E. Fazio. Materials.,15, 282, (2021).
[12]. B.L. Keller, A. Lohmann, S. Kyeremateng, G. Fricker, Polymers,14, 998 (2022).

[13]. A. Oucif, H. Nabila, Z. Dria, B. Naima, A. Benaboura, Kh. Beyaz, B. Guedouar, M.
Samy, Polym.Bull.79, 1554 (2022).
[14]. E. Adibzadeh, S.M. Mirabedini, F. Alizadegan, S. Dolatshah, R. Farnood, Colloids Surf. A:
Physicochem. Eng. Asp.,627, 127139 (2021).
[15]. R. Giuseppe, R. Palucci, A. Rossella, G. Malucelli, J. Appl. Polym. Sci.,138, 51292 (2021).
[16]. F. Kang, Ni. Chunhua, L. Yu, W. Zhou, Xi. Li, Colloids Surf. B: Biointerfaces,184,
110518 (2019).
[17]. R. Juan, R. Jaime Charris, R. Ferrer, N. Gamboa, J. Angel, B. Nitzsche, M. Hoepfner, M. Lein,
K. Jung, C. Abramjuk, Invest. New Drugs,30, 1426 (2012).
[18]. B. Soumen, P. Kumar, Sh. Singh, Sh.M. Mobin, S. Samanta, Org.Biomol.Chem.,11,
7087 (2013).
[19]. B. Neelaiah, A. Tadesse, A. Wote, V. Basker, Med. Chem. Res.,29, 416 (2020).
[20]. M. Silvija, P. Grbcic, S. Shammugam, M.R. Stojkovic, K. Pavelic, M. Sedic, S.K. Pavelic, S.
Raic-Malic, Molecules,26, 7060 (2021).
[21]. R. Mizzanoor, M. Shahnawaz, A. Khorshada, J. B. Belayet, R. Towheedur, M. Mahmun
Hossain, Org.Chem.Front., 8, 191 (2021).
[22]. M. Baumann, I.R. Baxendale, Beilstein J.Org.Chem.,9, 2319 (2013).
[23]. M. Hawata, A.S. Wael, E.S. Nossier, A. Abdel-Rahman, Biointerface Res. Appl Chem.,12,
5233 (2022).
[24]. A. Prashant S.G. Ginson, T.P. Atish, RSC Advances,10, 41392 (2020).
[25]. A. El-Sayed, A., Mahmoud, F. Ismail, A. El-Galil, A. Naglah, Molecules, 24, 3787 (2019).
[26]. A. Mostafa, A. Aziz, Sh. Wesam, M.H. Abdellattif, S.M. Mouneir, J.Saudi
Chem.Soc.,25, 101259 (2021).
[27]. H. Hajar, M. Bayat, RSC advances,8, 27143 (2018).
[28]. Kh. Ishaat, S. Shakya, R. Akhtar, A. Kehkashan, I. Maidul, A. Nisat, Bioorg.Chem.,100,
103872 (2020).
[29]. M. Flores-Sumoza, J. Maryury, J. Alcazar, E. Marquez, R. Jose, M.J. Lezama, P. Esneyder,
Molecules,23, 3166 (2018).
[30]. V. Khodaverdian, S. Tapadar, I. MacDonald, Xu.Yuan, P. Yi-Ho, A. Bridges, P.
Rajpurohit, Sci.Rep.,9, 17 (2019).
[31]. J. Vaitekunas, R. Gasparaviciute, J. Stankeviciute, G. Urbelis, Microorganisms,8, 888 (2020).

[32]. A. Jafari, A. Ramazani, P. Azimzadeh Asiabi, F. Sadri, S.W. Joo, Phosphorus Sulfur
SiliconRelat.Elem.,190, 2246 (2015). 

[33]. A, Ramazani, F. Zeinali Nasrabdi, A. Mashhadi Malekzadeh, Y. Ahmadi, Monatsh.Chem.,142,
625 (2011).
[34]. B. Mohtat, Z. Najafi Azar, S. Nahavandian, H. Djahaninai, A. Ahmadi, J. Mex. Chem.
Soc.,55, 194 (2011).
[35]. M. Bazaz Rastkar, B. Mohtat, NSMSI.,38, 177 (2019).
[36]. B. Mohtat, S. Jabbar, A. Ghasemi, I. Yavari, J. Chem. Res., 10, 601 (2008).
[37]. B. Mohtat H. Djahaniani, Iran. J. Org. Chem.,7, 1473 (2015).
[38]. B. Mohtat, S. Azimzadeh, H. Djahaniani, L. Pirhadi,S. Afr. J. Chem.,63, 204 (2010).
[39]. I.Yavari, A.R. Alborzi, B. Mohtat, J. Chem. Res.,7, 397 (2007).
[40]. E. Pretsch, P. Buhlmann, M. Badertscher, Structure Determination of Organic
Compounds, Springer Verlag, Berlin, (2009).
[41]. A. Dmling,Chem. Rev.,106, 89 (2006).