European Journal of Chemistry 2014, 5(1), 167-170. doi:10.5155/eurjchem.5.1.167-170.917

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


Vijay Manneganti (1) , Badari Narayana Prasad Rachapudi (2) , Lakshmi Anu Prabhavathi Devi Bethala (3,*)

(1) Centre for Lipid Research, CSIR Indian Institute of Chemical Technology, Hyderabad-500 007, India
(2) Centre for Lipid Research, CSIR Indian Institute of Chemical Technology, Hyderabad-500 007, India
(3) Centre for Lipid Research, CSIR Indian Institute of Chemical Technology, Hyderabad-500 007, India
(*) Corresponding Author

Received: 05 Sep 2013, Accepted: 02 Nov 2013, Published: 31 Mar 2014

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.


Keywords


Water; Oxiranes; Azidolysis; Sodium azide; Azidohydrins; Carbon acid catalyst

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DOI: 10.5155/eurjchem.5.1.167-170.917

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[2]. G. Sandhya Rani, Manneganti Vijay, Bethala L. A. Prabhavathi Devi
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[3]. Chandrakala Ummadisetti, Badari Narayana Prasad Rachapudi, Lakshmi Anu Prabhavathi Devi Bethala
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[5]. Siyi Zhang, Junqiao Li, Genzhong Ji, Xuezheng Liang
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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.


How to cite


Manneganti, V.; Rachapudi, B.; Bethala, L. Eur. J. Chem. 2014, 5(1), 167-170. doi:10.5155/eurjchem.5.1.167-170.917
Manneganti, V.; Rachapudi, B.; Bethala, L. SO3H-Carbon derived from glycerol: An efficient and recyclable catalyst for smooth and regioselective azidolysis of oxiranes in water. Eur. J. Chem. 2014, 5(1), 167-170. doi:10.5155/eurjchem.5.1.167-170.917
Manneganti, V., Rachapudi, B., & Bethala, L. (2014). SO3H-Carbon derived from glycerol: An efficient and recyclable catalyst for smooth and regioselective azidolysis of oxiranes in water. European Journal of Chemistry, 5(1), 167-170. doi:10.5155/eurjchem.5.1.167-170.917
Manneganti, Vijay, Badari Narayana Prasad Rachapudi, & Lakshmi Anu Prabhavathi Devi Bethala. "SO3H-Carbon derived from glycerol: An efficient and recyclable catalyst for smooth and regioselective azidolysis of oxiranes in water." European Journal of Chemistry [Online], 5.1 (2014): 167-170. Web. 16 Sep. 2019
Manneganti, Vijay, Rachapudi, Badari, AND Bethala, Lakshmi. "SO3H-Carbon derived from glycerol: An efficient and recyclable catalyst for smooth and regioselective azidolysis of oxiranes in water" European Journal of Chemistry [Online], Volume 5 Number 1 (31 March 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.1.167-170.917

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