Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Efficient and Regioselective Ring-opening of Epoxides with Carboxylic Acid Catalyzed by Graphite Oxide

Author(s): Maryam Mirza-Aghayan*, Mahdieh Molaee Tavana, Elaheh Golam Alipour Niazi and Rabah Boukherroub

Volume 17, Issue 7, 2020

Page: [532 - 538] Pages: 7

DOI: 10.2174/1570178616666190401194252

Price: $65

Abstract

An efficient, simple and regioselective ring-opening reaction of epoxides with various carboxylic acids under metal-free conditions is reported. The ring-opening of epoxides takes place in the presence of graphite oxide as an efficient and available catalyst to produce the corresponding 2-hydroxy monoester and 1,2-diester derivatives in good yields. Regioselective attack of the nucleophile, short reaction times, metal-free conditions and reusability of catalyst are among the advantages of the present protocol.

Keywords: Ring-opening, epoxides, carboxylic acids, metal-free conditions, graphite oxide, 1, 2-diester.

« Previous Next »
Graphical Abstract

[1]
Robinson, M.W.; Buckle, R.; Mabbett, I.; Grant, G.M.; Graham, A.E. Tetrahedron Lett., 2007, 48, 4723-4725.
[2]
Yadav, G.D.; Surve, P.S. Ind. Eng. Chem. Res., 2013, 52, 6129-6137.
[3]
Yadav, G.D.; Surve, P.S. Catal. Sci. Technol., 2013, 3, 2668-2676.
[4]
Taghavi, S.A.; Moghadam, M.; Mohammadpoor-Baltork, I.; Tangestaninejad, S.; Mirkhani, V.; Khosropour, A.R.; Ahmadi, V. Polyhedron, 2011, 30, 2244-2252.
[5]
Yadav, G.D.; Surve, P.S. Appl. Catal. A, 2013, 468, 112-119.
[6]
Ellis, B. In chemistry and technology of epoxy resins, blackie academic and professional; London, 1993.
[7]
Tokunaga, M.; Larrow, J.F.; Kakiuchi, F. Science, 1997, 277, 936-938.
[8]
Fan, R-H.; Hou, X-L. Tetrahedron Lett., 2003, 44, 4411-4413.
[9]
Das, B.; Reddy, V.S.; Tehseen, F. Tetrahedron Lett., 2006, 47, 6865-6868.
[10]
Watson, K.G.; Fung, Y.M.; Gredley, M.; Bird, G.J.; Jackson, W.R.; Gountzos, H.; Mattews, V.A. J. Chem. Soc. Chem. Commun., 1990, 1018-1019.
[11]
Kolb, H.C.; Sharpless, K.B. Tetrahedron, 1992, 48, 10515-10530.
[12]
Prasad, B.B.; Sekar, G.; Singh, V.K. Tetrahedron Lett., 2000, 41, 4677-4679.
[13]
Mirkhani, V.; Tangestaninejad, S.; Yadollahi, B.; Alipanah, L. Tetrahedron, 2003, 59, 8213-8218.
[14]
Cheudary, B.M.; Sudha, Y. Synth. Commun., 1996, 26, 2989-2992.
[15]
Yarapathi, R.V.; Reddy, S.M.; Tammishetti, S. React. Funct. Polym., 2005, 64, 157-161.
[16]
Thakur, S.S.; Chen, S.-W.; Li, W.; Shin, C.-K.; Kim, S.-J.; Koo, Y.-M.; Kim, G.-J. J. Organomet. Chem., 2006, 691, 1862-1872.
[17]
Tangestaninejad, S.; Moghadam, M.; Mirkhani, V.; Yadollahi, B.; Mirmohammadi, S.M.R. Monatsh. Chem., 2006, 137, 235-242.
[18]
Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mohammadpoor-Baltork, I.; Taghavi, S.A. Catal. Commun., 2007, 8, 2087-2095.
[19]
Li, W.; Thakur, S.S.; Chen, S-W.; Shin, C-K.; Kawthekar, R.B.; Kim, G-J. Tetrahedron Lett., 2006, 47, 3453-3457.
[20]
Kim, J.W.; Cho, D.W.; Park, G.; Kim, S.H.; Ra, C.S. Bull. Korean Chem. Soc., 2013, 34, 2287-2290.
[21]
Iranpoor, N.; Baltork, I.M. Synth. Commun., 1990, 20, 2789-2797.
[22]
Iranpoor, N.; Baltork, I.M. Tetrahedron Lett., 1990, 31, 735-738.
[23]
Iranpoor, N.; Baltork, I.M.; Shiriny Zardaloo, F. Tetrahedron Lett., 1991, 47, 9861-9866.
[24]
Ollevier, T.; Lavie-Compin, G. Tetrahedron, 2002, 43, 7891-7893.
[25]
Neef, G.; Ottow, E.; Ast, G.; Vierhufe, H. Synth. Commun., 1993, 23, 903-911.
[26]
Spiro, M. Catal. Today, 1990, 71, 167-178.
[27]
Dreyer, D.R.; Bielawski, C.W. Chem. Sci., 2011, 2, 1233-1240.
[28]
Kumar, A.V.; Rao, K.R. Tetrahedron Lett., 2011, 52, 5188-5191.
[29]
Mirza-Aghayan, M.; Kashef-Azar, E.; Boukherroub, R. Tetrahedron Lett., 2012, 53, 4962-4965.
[30]
Mirza-Aghayan, M.; Molaee Tavana, M.; Boukherroub, R. Tetrahedron Lett., 2014, 55, 342-345.
[31]
Mirza-Aghayan, M.; Boukherroub, R.; Nemati, M.; Rahimifard, M. Tetrahedron Lett., 2012, 53, 2473-2475.
[32]
Mirza-Aghayan, M.; Asadi, F.; Boukherroub, R. Monatsh. Chem., 2014, 145, 1919-1924.
[33]
Mirza-Aghayan, M.; Boukherroub, R.; Rahimifard, M. Turk. J. Chem., 2014, 38, 859-864.
[34]
Mirza-Aghayan, M.; Alizadeh, M.; Molaee Tavana, M.; Boukherroub, R. Tetrahedron Lett., 2014, 55, 6694-6697.
[35]
Firouzabadi, H.; Iranpoor, N.; Jafari, A.A.; Makaremm, S. J. Mol. Catal., 2006, 250, 237-242.
[36]
Bradley, G.; Williams, D.; Lawton, M. Org. Biomol. Chem., 2005, 3, 3269-3272.
[37]
Kim, B.H.; Piao, F.; Lee, E.J.; Kim, J.S.; Jun, Y.M.; Lee, B.M. Bull. Korean Chem. Soc., 2004, 25, 881-888.
[38]
Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Shaibani, R. Tetrahedron, 2004, 60, 6105-6111.
[39]
Chen, J.; Liu, D.; Butt, N.; Li, C.; Fan, D.; Liu, Y.; Zhang, W. Angew. Chem. Int, 2013, 52, 11632-11636.
[40]
Manzocchi, A.; Fiecchi, A.; Santaniello, E. J. Org. Chem., 1988, 53, 4405-4407.
[41]
Parmar, V.; Sinha, R.; Bisht, K.; Gupta, S.; Prasad, A.; Taneja, P. Tetrahedron, 1993, 49, 4107-4116.
[42]
Poppe, L.; Nevik, J.L. Tetrahedron Asymmetry, 1993, 4, 2211-2217.
[43]
Schønheyder, F.; Volqvartz, K. Biochim. Biophys. Acta, 1952, 8, 407-415.
[44]
Magnusson, C.D.; Haraldsson, G.G. Tetrahedron, 2010, 66, 2728-2731.
[45]
Tian, X.; Zheng, G-W.; Li, C-X.; Wang, Z-L.; Xu, J-H. J. Mol. Catal., B., 2011, 73, 80-84.
[46]
Montaudon, E.; Rakotomanana, F.; Mailiard, B. Tetrahedron, 1985, 41, 2727-2735.
[47]
Jie, M.S.L.K.; Lam, C. Chem. Phys. Lipids, 1995, 77, 155-171.
[48]
Mereyala, H.B.; Mamidyala, S.K.; Chigurupati, K.P.; Srinivasa, S.R. Synthesis, 2003, 2378-2384.

Rights & Permissions Print Cite
Article Metrics
26
© 2024 Bentham Science Publishers | Privacy Policy