European Journal of Chemistry 2014, 5(3), 541-544. doi:10.5155/eurjchem.5.3.541-544.1049

Aqueous phase synthesis of polysubstituted pyrimidines/pyrrolidines catalyzed by β-cyclodextrin


Jilla Shankar (1) , Gaddam Satish (2) , Katla Ramesh (3) , Nageswar Yadavalli Venkata Durga (4,*)

(1) Council of Scientific and Industrial Research-Medicinal Chemistry and Pharmacology Division, Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500-007, India
(2) Council of Scientific and Industrial Research-Medicinal Chemistry and Pharmacology Division, Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500-007, India
(3) Council of Scientific and Industrial Research-Medicinal Chemistry and Pharmacology Division, Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500-007, India
(4) Council of Scientific and Industrial Research-Medicinal Chemistry and Pharmacology Division, Indian Institute of Chemical Technology, Uppal Road, Hyderabad 500-007, India
(*) Corresponding Author

Received: 13 Mar 2014, Accepted: 22 Apr 2014, Published: 30 Sep 2014

Abstract


Highly substituted pyrimidine/pyrrolidine derivatives were synthesized for the first time in water under neutral conditions by the reaction of aromatic amines, dimethyl/diethyl acetylene dicarboxylates, formaldehyde mediated by β-cyclodextrin (β-CD) in good to excellent yields. β-Cyclodextrin can be recovered and reused without any loss of catalytic activity. The β-Cyclodextrins employed were inexpensive and readily available when compared to other types of cyclodextrins (α, γ).


Keywords


Amines; Formaldehyde; β-Cyclodextrin; Pyrimidine derivatives; Pyrrolidine derivatives; Dimethyl/diethyl acetylene dicarboxylates

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.3.541-544.1049

Article Metrics


This Abstract was viewed 524 times | PDF Article downloaded 192 times

Citations

/


[1]. Mohsen Abbasi
β-Cyclodextrin as an Efficient and Recyclable Supramolecular Catalyst for the Synthesis of Heterocyclic Compounds
Journal of the Chinese Chemical Society  64(8), 896, 2017
DOI: 10.1002/jccs.201600887
/


[2]. Soumyadip Basu, Tanushree Ghosh, Suvendu Maity, Prasanta Ghosh, Chhanda Mukhopadhyay
An Efficient Phosphotungstic Acid Catalysed Synthesis of 4,5‐Dioxopyrrolidines and Study of the Mechanistic Effect of the Solvent on the Reaction
ChemistrySelect  4(19), 5763, 2019
DOI: 10.1002/slct.201901011
/


References

[1]. Sondhi, S. M.; Jain, S.; Dinodia, M.; Shuklab, R.; Raghubir, R. Bioorg. Med. Chem. 2007, 15, 3334-3344.
http://dx.doi.org/10.1016/j.bmc.2007.03.028

[2]. Srivastav, N. C.; Manning, T. D.; Kunimoto, Y.; Kumar, R. Bioorg. Med. Chem. 2007, 15, 2045-2053.
http://dx.doi.org/10.1016/j.bmc.2006.12.032

[3]. Gazivoda, T.; Plevnik, M.; Plavec, J.; Kraljevic, S.; Kralj, M.; Pavelic, K.; Balzarini, J.; Clercq, E. D.; Mintasa, M.; Silvana, R. Bioorg. Med. Chem. 2005, 13, 131-139.
http://dx.doi.org/10.1016/j.bmc.2004.09.052

[4]. Tozkoparan, B.; Yarim, M.; Sarac, S.; Ertan, M.; Kelicen, P.; Altinok, G.; Demirdamar, R. Arch. Pharm. 2000, 333, 415-420.
http://dx.doi.org/10.1002/1521-4184(200012)333:12<415::AID-ARDP415>3.0.CO;2-E

[5]. DeLucca, G. V.; Liang, J.; De Lucca, I. J. Med. Chem. 1999, 42, 135-152.
http://dx.doi.org/10.1021/jm9803626

[6]. Dunbar, P. G.; Durant, G. J.; Rho, T.; Ojo, B.; Huzl, J. J.; Smith, D. A.; A El-Assadi, M.; Sbeih, S.; Ngur, D. O.; Periyasamy, S.; Hoss, W.; Messer, W. S. J. Med. Chem. 1994, 37, 2774-2782.
http://dx.doi.org/10.1021/jm00043a016

[7]. Muravyova, E. A.; Desenko, S. M.; Musatov, V. I.; Knyazeva, I. V.; Shishkina, S. V.; Shishkin, O. V.; Chebanov, V. A. J. Comb. Chem. 2007, 9, 797-803.
http://dx.doi.org/10.1021/cc700089a

[8]. Swinbourne, J. F.; Hunt, H. J.; Klinkert, G. Adv. Heterocycl. Chem. 1987, 23, 103-170.
http://dx.doi.org/10.1016/S0065-2725(08)60842-9

[9]. Hermecz, I.; Vasvari-Debreczy, L.; Matyus, P. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.;Rees, C. W.; Scriven, E. V. F. Eds.; Pergamon: London, 1996; Chapter 8.23, pp. 563-595.

[10]. Nair, A. C.; Jayatilleke, P.; Wang, X.; Miertus, S.; Welsh, W. J. Med. Chem. 2002, 45, 973-982.
http://dx.doi.org/10.1021/jm010417v

[11]. Zamri, A.; Sirockin, F.; Abdallah, M. A. Tetrahedron 1999, 55, 5157-5170.
http://dx.doi.org/10.1016/S0040-4020(99)00177-5

[12]. Shutalev, A. D.; Fesenko, A. A.; Cheshkov, D. A.; Goliguzov, D. V. Tetrahedron Lett. 2008, 49, 4099-4101.
http://dx.doi.org/10.1016/j.tetlet.2008.04.136

[13]. Mohrle, H.; Reinhardt, H. W. Arch. Pharm. 1981, 314, 767-776.
http://dx.doi.org/10.1002/ardp.19813140907

[14]. Cho, H.; Shima, K.; Hayashimatsu, M.; Ohnaka, Y.; Mizuno, A.; Takeuchi, Y. J. Org. Chem. 1985, 50, 4227-4230.
http://dx.doi.org/10.1021/jo00222a009

[15]. Zhang, M.; Jiang, H. -F. J.; Liu, H. L.; Zhu, Q. H. Org. Lett. 2007, 9, 4111-4113.
http://dx.doi.org/10.1021/ol701592h

[16]. Chanda, K.; Dutta, Ch. M.; Karim, E.; Vishwakarma J. N. J. Heterocyclic.Chem. 2004, 41, 627-631.
http://dx.doi.org/10.1002/jhet.5570410425

[17]. Das, B.; Shinde, D. B.; ShashiKanth, B.; Satyalakshmi, G. Synthesis. 2010, 16, 2823-2825.
http://dx.doi.org/10.1055/s-0030-1258138

[18]. Zhu, Q.; Jiang, H.; Li, J.; Zhang, M.; Wang, X.; Qi, C. Tetrahedron 2009, 65, 4604-4613.
http://dx.doi.org/10.1016/j.tet.2009.03.071

[19]. Shankar, J.; Karnakar, K.; Srinivas, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3938-3939.
http://dx.doi.org/10.1016/j.tetlet.2010.05.096

[20]. Ramesh, K.; Murthy, S. N.; Nageswar, Y. V. D. Tetrahedron Lett. 2011, 52, 2362-2366.
http://dx.doi.org/10.1016/j.tetlet.2011.02.082

[21]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2011, 52, 3937-3941.
http://dx.doi.org/10.1016/j.tetlet.2011.05.100

[22]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2011, 52, 4734-4737.
http://dx.doi.org/10.1016/j.tetlet.2011.06.098

[23]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D.; Vijayalakhshmi, K.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 44, 1126-1129.
http://dx.doi.org/10.1016/j.tetlet.2011.12.092

[24]. Ramesh, K.; Karnakar, K.; Satish, G.; Reddy, K. H. V.; Nageswar, Y. V. D. Tetrahedron Lett. 2012, 53, 6095-6099.
http://dx.doi.org/10.1016/j.tetlet.2012.08.141

[25]. Ramesh, K.; Karnakar, K.; Satish, G.; Anil Kumar, B. S. P.; Nageswar, Y. V. D. Tetrahedron Lett. 2012, 53, 6936-6939.
http://dx.doi.org/10.1016/j.tetlet.2012.10.029

[26]. Ramesh, K.; Karnakar, K.; Satish, G.; Nageswar, Y. V. D. Chin. Chem. Lett. 2012, 23, 1331-1334.
http://dx.doi.org/10.1016/j.cclet.2012.11.005

[27]. Ramesh, K.; Narayana Murthy, S.; Karnakar, K.; Nageswar, Y. V. D. Eur. J. Chem. 2012, 3(1), 119-124.
http://dx.doi.org/10.5155/eurjchem.3.1.119-124.449


How to cite


Shankar, J.; Satish, G.; Ramesh, K.; Durga, N. Eur. J. Chem. 2014, 5(3), 541-544. doi:10.5155/eurjchem.5.3.541-544.1049
Shankar, J.; Satish, G.; Ramesh, K.; Durga, N. Aqueous phase synthesis of polysubstituted pyrimidines/pyrrolidines catalyzed by β-cyclodextrin. Eur. J. Chem. 2014, 5(3), 541-544. doi:10.5155/eurjchem.5.3.541-544.1049
Shankar, J., Satish, G., Ramesh, K., & Durga, N. (2014). Aqueous phase synthesis of polysubstituted pyrimidines/pyrrolidines catalyzed by β-cyclodextrin. European Journal of Chemistry, 5(3), 541-544. doi:10.5155/eurjchem.5.3.541-544.1049
Shankar, Jilla, Gaddam Satish, Katla Ramesh, & Nageswar Yadavalli Venkata Durga. "Aqueous phase synthesis of polysubstituted pyrimidines/pyrrolidines catalyzed by β-cyclodextrin." European Journal of Chemistry [Online], 5.3 (2014): 541-544. Web. 17 Sep. 2019
Shankar, Jilla, Satish, Gaddam, Ramesh, Katla, AND Durga, Nageswar. "Aqueous phase synthesis of polysubstituted pyrimidines/pyrrolidines catalyzed by β-cyclodextrin" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.3.541-544.1049

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.