European Journal of Chemistry

SO3H-Carbon derived from glycerol: An efficient and recyclable catalyst for smooth and regioselective azidolysis of oxiranes in water



Main Article Content

Vijay Manneganti
Badari Narayana Prasad Rachapudi
Lakshmi Anu Prabhavathi Devi Bethala

Abstract

A series of β-hydroxyazides were effectively synthesized from the regioselective ring opening of oxiranes by azide anion in presence of glycerol-based sulfonic acid functionalized carbon as a novel reusable heterogeneous catalyst in H2O achieving good yields (80-98%). The workup procedure was simple, and the catalyst could be reused over five times without losing its catalytic activity and selectivity.


icon graph This Abstract was viewed 1553 times | icon graph Article PDF downloaded 855 times

How to Cite
(1)
Manneganti, V.; Rachapudi, B. N. P.; Bethala, L. A. P. D. SO3H-Carbon Derived from Glycerol: An Efficient and Recyclable Catalyst for Smooth and Regioselective Azidolysis of Oxiranes in Water. Eur. J. Chem. 2014, 5, 167-170.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Fringuelli, F.; Piermatti, O.; Pizzo, F. Trends Org. Chem. 1997, 6, 181-197.

[2]. Smith, J. G. Synthesis 1984, 8, 629-656.
http://dx.doi.org/10.1055/s-1984-30921

[3]. Iranpoor, N.; Mohammadpour, B. I. Synth. Commun. 1990, 20, 2789-2797.
http://dx.doi.org/10.1080/00397919008051491

[4]. Shimizu, M.; Yoshida, A.; Fujisawa, T. Synlett 1992, 3, 204-206.
http://dx.doi.org/10.1055/s-1992-21314

[5]. Bonini, C.; Righi, G. Synthesis 1994, 3, 225-238.
http://dx.doi.org/10.1055/s-1994-25445

[6]. Olah, G.; Fung, A. P.; Meidar, D. Synthesis 1981, 4, 280-282.
http://dx.doi.org/10.1055/s-1981-29414

[7]. Otera, J.; Yashinaga, Y.; Hirakawa, K.; Nakata, T. Tetrahedron Lett. 1985, 26, 3219-3222.
http://dx.doi.org/10.1016/S0040-4039(00)98156-5

[8]. Chini, M.; Crott, P.; Cardelli, C.; Macchina, F. Synlett, 1992, 8, 673-676.
http://dx.doi.org/10.1055/s-1992-21454

[9]. Tamami, B.; Iranpoor, N.; Karimizarchi, M. A. Polymer 1993, 34, 2011-2013.
http://dx.doi.org/10.1016/0032-3861(93)90457-L

[10]. Iranpoor, N.; Firouzabadi, H.; Safavi, A.; Shakarrize, M. Synth. Commun. 2002, 32, 2287-2293.
http://dx.doi.org/10.1081/SCC-120005998

[11]. Scriveni, E. F. V.; Turnbull, K. Chem. Rev. 1988, 88, 297-368.
http://dx.doi.org/10.1021/cr00084a001

[12]. Chini, M.; Crotti, P.; Favero, L.; Macchina, F.; Pineschi, M. Tetrahedron Lett, 1994, 35, 433-436.
http://dx.doi.org/10.1016/0040-4039(94)85073-9

[13]. Iranpoor, N.; Salehi, P. Tetrahedron 1995, 51, 909-912.
http://dx.doi.org/10.1016/0040-4020(94)00979-5

[14]. Tamami, B.; Ghazi, I.; Mahdavi, H. Synth. Commun. 2002, 32, 3725-3731.
http://dx.doi.org/10.1081/SCC-120015389

[15]. Ciaccio, A.; Stanescu, C.; Bontemps, J. Tetrahedron. Lett. 1992, 33, 1431-1434.
http://dx.doi.org/10.1016/S0040-4039(00)91639-3

[16]. Patai, S., The Chemistry of the Azido Group, Ed; Wiley: New York, 1971.

[17]. Coe, D. M.; Myers, P. L.; Parry, D. M.; Roberts, S. M.; Storerb, R. J. Chem. Soc. Chem. Comm. 1990, 2, 151-153.
http://dx.doi.org/10.1039/c39900000151

[18]. Schubert, J.; Schwesinger, R.; Prinzbach, H. Angew. Chem. Int. Ed. 1984, 23, 167-169.
http://dx.doi.org/10.1002/anie.198401671

[19]. Boruwa, J.; Borah, J. C.; Kalita, B.; Barua, N. C. Tetrahedron Lett. 2004, 45, 7355-7358.
http://dx.doi.org/10.1016/j.tetlet.2004.07.157

[20]. Serrano, P.; Liebaria, A.; Delgado, A. J. Org. Chem. 2002, 67, 7165-7167.
http://dx.doi.org/10.1021/jo0261146

[21]. Amantini, F.; Fringuelli, O.; Piermatti, S.; Tortiioli, L.; Vaccaro, L. Arkivoc 2002, 11, 293-311.

[22]. Spelberg, J. H. L.; Vlieg, J. E. T. H.; Tang, L.; Janssen, D. B.; Kellogg, R. M. Org. Lett. 2001, 3, 41-43.
http://dx.doi.org/10.1021/ol0067540

[23]. Yadollahi, B.; Danafar, H. Catal. Lett. 2007, 113, 120-123.
http://dx.doi.org/10.1007/s10562-007-9021-0

[24]. Kazemi, F.; Kiasat, A. R.; Ebrahimi, S. Synth. Commun. 2003, 33, 999-1004.
http://dx.doi.org/10.1081/SCC-120016364

[25]. Sarangi, C.; Das, N. B.; Nanda, B.; Nayak, A.; Sharma, R. P. J. Chem. Research (S) 1997, 10, 378-379.
http://dx.doi.org/10.1039/a701358b

[26]. Sabitha, G.; Babu, R. S.; Rajkumar, M.; Yadav, J. S. Org. Lett. 2002, 4, 343-345.
http://dx.doi.org/10.1021/ol016979q

[27]. Chini, M.; Crotti, P.; Macchia, F. Tetrahedron Lett. 1990, 31, 5641-5644.
http://dx.doi.org/10.1016/S0040-4039(00)97921-8

[28]. Saito, S.; Yamashita, S.; Nishikawa, T.; Yokoyama, Y.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 4153-4156.
http://dx.doi.org/10.1016/S0040-4039(00)99346-8

[29]. Saito, S.; Nishikawa, T.; Yokoyama, Y.; Moriwake, T. Tetrahedron Lett. 1990, 31, 221-224.
http://dx.doi.org/10.1016/S0040-4039(00)94376-4

[30]. Benedetti, F.; Berti, F.; Norbedo, S. Tetrahedron Lett. 1998, 39, 7971-7974.
http://dx.doi.org/10.1016/S0040-4039(98)01733-X

[31]. Maruoka, K.; Sano, H.; Yamamoto, H. Chem. Lett. 1985, 14, 599-602.
http://dx.doi.org/10.1246/cl.1985.599

[32]. Davis, C. E.; Bailey, J. L.; Lockner, J. W.; Coates, R. M. J. Org. Chem. 2003, 68, 75-82.
http://dx.doi.org/10.1021/jo026506c

[33]. Tamami, B.; Iranpoor, N.; Rezaie, R. Iran. Polym. J. 2004, 13, 495-501.

[34]. Kiasat, A. R.; Badri, R.; Zargar, B.; Sayyahi, S. J. Org. Chem. 2008, 73, 8382-8385.
http://dx.doi.org/10.1021/jo801356y

[35]. Sabitha, G.; Babu, R. S.; Reddy, M. S. K.; Yadav, J. S. Synthesis 2002, 15, 2254-2258.
http://dx.doi.org/10.1055/s-2002-34848

[36]. Onaka, M.; Sugit, K.; Izumi, Y. Chem. Lett. 1986, 15, 1327-1328.
http://dx.doi.org/10.1246/cl.1986.1327

[37]. Das, B.; Reddy, V. S.; Krishnaiah, M.; Rao, Y. K. J. Mol. Cat. A: Chem. 2007, 270, 89-92.
http://dx.doi.org/10.1016/j.molcata.2007.01.040

[38]. Schneider, C. Synlett 2000, 12, 1840-1842.

[39]. Tamami, B.; Mahdavi, H. Tetrahedron Lett. 2001, 42, 8721-8724.
http://dx.doi.org/10.1016/S0040-4039(01)01891-3

[40]. Wang, Z.; Cui, Y. T.; Xu, Z. B.; Qu, J.; J. Org. Chem. 2008, 73, 2270-2274.
http://dx.doi.org/10.1021/jo702401t

[41]. Hara, M.; Yoshida, T.; Takagaki, A.; Takata, T.; Kondo, J. N.; Hayashi, S.; Domen, K. Angew. Chem. Int. Ed. 2004, 43, 2955-2958.
http://dx.doi.org/10.1002/anie.200453947

[42]. Toda, M.; Takagaki, A.; Okamura, M.; Ondo, J. N.; Domen, K.; Hayashi, S.; Hara, M. Nature 2005, 438, 178-178.
http://dx.doi.org/10.1038/438178a

[43]. Takagaki, A.; Toda, M.; Okamura, M.; Kondo, J. N.; Hayashi, S.; Domen, K.; Hara, M. Catal. Today 2006, 116, 157-161.
http://dx.doi.org/10.1016/j.cattod.2006.01.037

[44]. Zong, M. H.; Duan, Z. Q.; Lou, W. Y.; Smith, T. J.; Wu, H. Green Chem. 2007, 9, 434-437.
http://dx.doi.org/10.1039/b615447f

[45]. Mo, X., Lopez, D. E.; Suwannakarn, K.; Liu, Y.; Lotero, E.; Goodwin, J. G.; Lu, C. J. Catal. 2008, 254, 332-338.
http://dx.doi.org/10.1016/j.jcat.2008.01.011

[46]. Prabhavathi, D. B. L. A.; Gangadhar, K. N.; Prasad, P. S. S.; Jagannadh, B.; Prasad, R. B. N. Chem. Sus. Chem. 2009, 2, 617-620.
http://dx.doi.org/10.1002/cssc.200900097

[47]. Prabhavaeti, D. B. L. A.; Gangadhar, K. N.; Kumar, K. L. N. S.; Sanker, K. S.; Prasad, R. B. N.; Prasad, P. S. S. J. Mol. Cat. A: Chem. 2011, 345, 96-100.
http://dx.doi.org/10.1016/j.molcata.2011.05.025

[48]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Nageswar, Y. V. D.; Vijayalakhsmi, K.; Prabhavaeti, D. B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1126-1129.
http://dx.doi.org/10.1016/j.tetlet.2011.12.092

[49]. Karnakar, K.; Murthy, S. N.; Ramesh, K.; Nageswar, Y. V. D.; Reddy, T. V. K.; Prabhavathi, D. B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 1968-1973.
http://dx.doi.org/10.1016/j.tetlet.2012.02.018

[50]. Ramesh, K.; Murthy, S. N.; Karnakar, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Vijay, M.; Prabhavaeti, D. B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 2636-2638.
http://dx.doi.org/10.1016/j.tetlet.2012.03.051

[51]. Karnakar, K.; Murthy, S. N.; Ramesh, K.; Reddy, K. H. V.; Nageswar, Y. V. D.; Chandrakala, U.; Prabhavathi, D. B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 3497-3501.
http://dx.doi.org/10.1016/j.tetlet.2012.04.122

[52]. Rao, B. M.; Reddy, G. N.; Reddy, T. V. K.; Prabhavathi, D. B. L. A.; Prasad, R. B. N.; Yadav, J. S.; Reddy, B. V. S.; Tetrahedron Lett. 2013, 54, 2466-2471.
http://dx.doi.org/10.1016/j.tetlet.2013.02.089

[53]. Gangadhar, K. N.; Vijay, M.; Prasad, R. B. N.; Prabhavathi, D. B. L. A. Green Sust. Chem. 2013, 3, 122-218.

Supporting Agencies

Council of Scientific and Industrial Research (CSIR), New Delhi, India
Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).