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1-Butyl-3-methylimidazol-2-ylidene as an Efficient Catalyst for Cross-Coupling between Aromatic Aldehydes and N-Aroylbenzotriazoles
Corresponding Author(s) : Baramee Phungpis
Asian Journal of Chemistry,
Vol. 33 No. 3 (2021): Vol 33 Issue 3
Abstract
Cross-coupling of aromatic aldehydes with N-aroylbenzotriazoles in [Bmim]Br in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) provided an efficient procedure for the synthesis of 1,2-diarylethane-1,2-diones.
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- V.F. Scalfani, A. Al Alshaikh and J.E. Bara, Ind. Eng. Chem. Res., 57, 15971 (2018); https://doi.org/10.1021/acs.iecr.8b02573
- S.T. Handy, Curr. Org. Chem., 9, 959 (2005); https://doi.org/10.2174/1385272054368411
- M.K. Potdar, M.S. Rasalkar, S.S. Mohile and M.M. Salunkhe, J. Mol. Catal. Chem., 235, 249 (2005); https://doi.org/10.1016/j.molcata.2005.04.007
- S.S. Mansoor, K. Aswin, K. Logaiya and S.P.N. Sudhan, J. Saudi Chem. Soc., 20, 517 (2016); https://doi.org/10.1016/j.jscs.2012.07.011
- A. Zare, A. Hasaninejad, A. Parhami, A.R. Moosavi-Zare, F. Khedri, Z. Parsaee, M. Abdolalipoor-Saretoli, M. Khedri, M. Roshankar and H. Deisi, J. Serb. Chem. Soc., 75, 1315 (2010); https://doi.org/10.2298/JSC091014109Z
- S. Sowmiah, V. Srinivasadesikan, M.-C. Tseng and Y.-H. Chu, Molecules, 14, 3780 (2009); https://doi.org/10.3390/molecules14093780
- L. Xu, W. Chen and J. Xiao, Organometallics, 19, 1123 (2000); https://doi.org/10.1021/om990956m
- V.K. Aggarwal, I. Emme and A. Mereu, Chem. Commun., 1612 (2002); https://doi.org/10.1039/b203079a
- S.M. Handy and M. Okello, J. Org. Chem., 70, 1915 (2005); https://doi.org/10.1021/jo0480850
- F.S. Jiang, H. Yu, G. Gao and R.G. Xie, Chinese Chem. Lett., 16, 321 (2005).
- B. Phungpis and V. Hahnvajanawong, Asian J. Chem., 32, 2028 (2020); https://doi.org/10.14233/ajchem.2020.22711
- B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Der Pharma Chem., 8, 167 (2016).
- S.-L. Zheng and P. Coppens, CrystEngComm, 7, 289 (2005); https://doi.org/10.1039/b502562a
- M. Hatanaka, C. Nishizawa, T. Kakinoki, K. Takahashi, S. Nakamura and T. Mashino, Bioorg. Med. Chem. Lett., 18, 5290 (2008); https://doi.org/10.1016/j.bmcl.2008.08.057
- G. Nithya, K. Charies C, R. Sudha, V. Vanitha, Int. J. Chem. Biol. Sci., 1, 25 (2015).
- V. Amita, J. Sunil, S. Deepika, J. Chem., 2013, 329412 (2013); https://doi.org/10.1155/2013/329412
- Y. Deepika, P.S. Nath, K. Sachin and S. Shewta, Int. J. Curr. Pharm. Rev. Res., 2, 33 (2011).
- D. Hernández-Romero, V.E. Torres-Heredia, O. García-Barradas, M.E. Márquez-López and E. Sánchez-Pavón, J. Chem. Biochem., 2, 45 (2014); https://doi.org/10.15640/jcb.v2n2a3
- A.-H. Ameen, Am. J. Org. Chem., 5, 14 (2015).
- V. Hahnvajanawong, B. Phungpis and P. Theramongkol, ACGC Chem. Res. Comm., 23, 26 (2009).
- V. Hahnvajanawong, W. Waengdongbung, S. Piekkaew, B. Phungpis and P. Theramongkol, Sci. Asia, 39, 50 (2013); https://doi.org/10.2306/scienceasia1513-1874.2013.39.050
- B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Orient. J. Chem., 30, 933 (2014); https://doi.org/10.13005/ojc/300303
- B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Der Pharma Chem., 8, 112 (2016).
- J. Buckingham, Dictionary of Organic Compounds, Chapman and Hall: New York, edn 5 (1982),
- https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0746966.htm.
- H. Firouzabadi, E. Mottghinejad and M. Seddighi, Synthesis, 378(1989); https://doi.org/10.1055/s-1989-27256
- https://www.guidechem.com/encyclopedia/1-4-methylphenyl-2-phenyl-etha-dic91029.html#id_-1584526519.
- https://www.fishersci.com/shop/products/4-4-dimethoxybenzil-99-acros-organics-2/AC170450050.
References
V.F. Scalfani, A. Al Alshaikh and J.E. Bara, Ind. Eng. Chem. Res., 57, 15971 (2018); https://doi.org/10.1021/acs.iecr.8b02573
S.T. Handy, Curr. Org. Chem., 9, 959 (2005); https://doi.org/10.2174/1385272054368411
M.K. Potdar, M.S. Rasalkar, S.S. Mohile and M.M. Salunkhe, J. Mol. Catal. Chem., 235, 249 (2005); https://doi.org/10.1016/j.molcata.2005.04.007
S.S. Mansoor, K. Aswin, K. Logaiya and S.P.N. Sudhan, J. Saudi Chem. Soc., 20, 517 (2016); https://doi.org/10.1016/j.jscs.2012.07.011
A. Zare, A. Hasaninejad, A. Parhami, A.R. Moosavi-Zare, F. Khedri, Z. Parsaee, M. Abdolalipoor-Saretoli, M. Khedri, M. Roshankar and H. Deisi, J. Serb. Chem. Soc., 75, 1315 (2010); https://doi.org/10.2298/JSC091014109Z
S. Sowmiah, V. Srinivasadesikan, M.-C. Tseng and Y.-H. Chu, Molecules, 14, 3780 (2009); https://doi.org/10.3390/molecules14093780
L. Xu, W. Chen and J. Xiao, Organometallics, 19, 1123 (2000); https://doi.org/10.1021/om990956m
V.K. Aggarwal, I. Emme and A. Mereu, Chem. Commun., 1612 (2002); https://doi.org/10.1039/b203079a
S.M. Handy and M. Okello, J. Org. Chem., 70, 1915 (2005); https://doi.org/10.1021/jo0480850
F.S. Jiang, H. Yu, G. Gao and R.G. Xie, Chinese Chem. Lett., 16, 321 (2005).
B. Phungpis and V. Hahnvajanawong, Asian J. Chem., 32, 2028 (2020); https://doi.org/10.14233/ajchem.2020.22711
B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Der Pharma Chem., 8, 167 (2016).
S.-L. Zheng and P. Coppens, CrystEngComm, 7, 289 (2005); https://doi.org/10.1039/b502562a
M. Hatanaka, C. Nishizawa, T. Kakinoki, K. Takahashi, S. Nakamura and T. Mashino, Bioorg. Med. Chem. Lett., 18, 5290 (2008); https://doi.org/10.1016/j.bmcl.2008.08.057
G. Nithya, K. Charies C, R. Sudha, V. Vanitha, Int. J. Chem. Biol. Sci., 1, 25 (2015).
V. Amita, J. Sunil, S. Deepika, J. Chem., 2013, 329412 (2013); https://doi.org/10.1155/2013/329412
Y. Deepika, P.S. Nath, K. Sachin and S. Shewta, Int. J. Curr. Pharm. Rev. Res., 2, 33 (2011).
D. Hernández-Romero, V.E. Torres-Heredia, O. García-Barradas, M.E. Márquez-López and E. Sánchez-Pavón, J. Chem. Biochem., 2, 45 (2014); https://doi.org/10.15640/jcb.v2n2a3
A.-H. Ameen, Am. J. Org. Chem., 5, 14 (2015).
V. Hahnvajanawong, B. Phungpis and P. Theramongkol, ACGC Chem. Res. Comm., 23, 26 (2009).
V. Hahnvajanawong, W. Waengdongbung, S. Piekkaew, B. Phungpis and P. Theramongkol, Sci. Asia, 39, 50 (2013); https://doi.org/10.2306/scienceasia1513-1874.2013.39.050
B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Orient. J. Chem., 30, 933 (2014); https://doi.org/10.13005/ojc/300303
B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Der Pharma Chem., 8, 112 (2016).
J. Buckingham, Dictionary of Organic Compounds, Chapman and Hall: New York, edn 5 (1982),
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0746966.htm.
H. Firouzabadi, E. Mottghinejad and M. Seddighi, Synthesis, 378(1989); https://doi.org/10.1055/s-1989-27256
https://www.guidechem.com/encyclopedia/1-4-methylphenyl-2-phenyl-etha-dic91029.html#id_-1584526519.
https://www.fishersci.com/shop/products/4-4-dimethoxybenzil-99-acros-organics-2/AC170450050.