European Journal of Chemistry 2014, 5(1), 167-170 | doi: https://doi.org/10.5155/eurjchem.5.1.167-170.917 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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 | Revised: 30 Oct 2013 | Accepted: 02 Nov 2013 | Published: 31 Mar 2014 | Issue Date: March 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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.1.167-170.917

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 712 times | PDF Article downloaded 358 times

Funding information


Council of Scientific and Industrial Research (CSIR), New Delhi, India

Citations

/


[1]. Sobhan Rezayati, Elaheh Salehi, Rahimeh Hajinasiri, Saeid Afshari Sharif Abad
Acetic acid functionalized ionic liquid systems: An efficient and recyclable catalyst for the regioselective ring opening of epoxides with NaN 3
Comptes Rendus Chimie  20(5), 554, 2017
DOI: 10.1016/j.crci.2016.07.004
/

[2]. G. Sandhya Rani, Manneganti Vijay, Bethala L. A. Prabhavathi Devi
SO 3 Cu‐Carbon: A Novel Heterogeneous Catalyst for the Synthesis of β‐Hydroxy 1,2,3‐Triazoles by One Pot Cycloaddition Reaction
ChemistrySelect  4(34), 10133, 2019
DOI: 10.1002/slct.201902289
/

[3]. Chandrakala Ummadisetti, Badari Narayana Prasad Rachapudi, Lakshmi Anu Prabhavathi Devi Bethala
Glycerol-based SO3H-Carbon Catalyst: A green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals
European Journal of Chemistry  5(3), 536, 2014
DOI: 10.5155/eurjchem.5.3.536-540.1028
/

[4]. Rathinam Ramesh, Gunasekaran Sankar, Jan Grzegorz Malecki, Appaswami Lalitha
Carbon–SO3H derived from glycerol: a green recyclable catalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones
Journal of the Iranian Chemical Society  15(1), 1, 2018
DOI: 10.1007/s13738-017-1202-1
/

[5]. Siyi Zhang, Junqiao Li, Genzhong Ji, Xuezheng Liang
One-pot synthesis of a novel magnetic carbon based solid acid for alkylation
Kinetics and Catalysis  58(4), 414, 2017
DOI: 10.1134/S002315841704005X
/

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. 17 Jan. 2020
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

| | | | |

| | | | | |

Save to Zotero Save to Mendeley

European Journal of Chemistry 2014, 5(1), 167-170 | doi: https://doi.org/10.5155/eurjchem.5.1.167-170.917 | Get rights and content

Refbacks

  • There are currently no refbacks.


Bookmark and Share


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.