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N-Aroylbenzotriazoles as Efficient Reagents for o-Aroylation in Absence of Organic Solvent
Corresponding Author(s) : Baramee Phungpis
Asian Journal of Chemistry,
Vol. 33 No. 11 (2021): Vol 33 Issue 11, 2021
Abstract
N-Aroylbenzotriazoles have been shown to be efficient reagents for esterification in the absence of organic solvent. Grinding of N-aroylbenzoytiazoles with twofold excess of alcohols for a couple of hours at room temperature gave corresponding esters in high percentage of yields.
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- A. Rodríguez, M. Nomen, B.W. Spur and J.J. Godfroid, Tetrahedron Lett., 39, 8563 (1998); https://doi.org/10.1016/S0040-4039(98)01958-3
- S. Feng, IOP Conf. Ser.: Earth Environ. Sci., 440, 022019 (2020); https://doi.org/10.1088/1755-1315/440/2/022019
- G. Bartoli, J. Boeglin, M. Bosco, M. Locatelli, M. Massaccesi, P. Melchiorre and L. Sambri, Adv. Synth. Catal., 347, 33 (2005); https://doi.org/10.1002/adsc.200404171
- T. Mineno and H. Kansui, Chem. Pharm. Bull. (Tokyo), 54, 918 (2006); https://doi.org/10.1248/cpb.54.918
- C.S. Cho, D.T. Kim, H.-J. Choi, T.-J. Kim and S.C. Shim, Bull. Korean Chem. Soc., 23, 539 (2002); https://doi.org/10.5012/bkcs.2002.23.4.539
- G.-S. Zhang, Synth. Commun., 28, 1159 (1998); https://doi.org/10.1080/00397919808005956
- G.V.M. Sharma, A.K. Mahalingam, M. Nagarajan, A. Ilangovan and P. Radhakrishna, Synlett, 1200 (1999); https://doi.org/10.1055/s-1999-2806
- R.N. Ram and I. Charles, Tetrahedron, 53, 7335 (1997); https://doi.org/10.1016/S0040-4020(97)00416-X
- N. Iranpoor, H. Firouzabadi and M.A. Zolfigol, Synth. Commun., 28, 1923 (1998); https://doi.org/10.1080/00397919808007166
- K. Ramalinga, P. Vijayalakshmi and T.N.B. Kaimal, Tetrahedron Lett., 43, 879 (2002); https://doi.org/10.1016/S0040-4039(01)02235-3
- B. Neises and W. Steglich, Angew. Chem. Int. Ed. Engl., 17, 522 (1978); https://doi.org/10.1002/anie.197805221
- K. Saigo, M. Usui, K. Kikuchi, E. Shimada and T. Mukaiyama, Bull. Chem. Soc. Jpn., 50, 1863 (1977); https://doi.org/10.1246/bcsj.50.1863
- K. Wakasugi, A. Nakamura, A. Iida, Y. Nishii, N. Nakatani, S. Fukushima and Y. Tanabe, Tetrahedron, 59, 5337 (2003); https://doi.org/10.1016/S0040-4020(03)00734-8
- A.R. Sardarian, M. Zandi and S. Motevally, Acta Chim. Slov., 56, 729 (2009).
- G. Höfle, W. Steglich and H. Vorbrüggen, Angew. Chem. Int. Ed. Engl., 17, 569 (1978); https://doi.org/10.1002/anie.197805691
- T. Sano, K. Ohashi and T. Oriyama, Synthesis, 1141 (1999); https://doi.org/10.1055/s-1999-3521
- K.L. Chandra, P. Saravanan, R.K. Singh and V.K. Singh, Tetrahedron, 58, 1369 (2002); https://doi.org/10.1016/S0040-4020(01)01229-7
- S.T. Heller, T. Fu and R. Sarpong, Org. Lett., 14, 1970 (2012); https://doi.org/10.1021/ol300339q
- A.R. Katritzky, H.-X. Chang and B. Yang, Synthesis, 503 (1995); https://doi.org/10.1055/s-1995-3959
- A.R. Katritzky, B. Yang and D. Semenzin, J. Org. Chem., 62, 726 (1997); https://doi.org/10.1021/jo961537r
- B. Phungpis and V. Hahnvajanawong, Asian J. Chem., 33, 651 (2021); https://doi.org/10.14233/ajchem.2021.23113
- B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Der Pharma Chem., 8, 167 (2016).
- B.S. Furniss, A.J. Hannaford, P.W.G. Smith and A.R. Tatchell, Vogel’s Textbook of practical Organic Chemistry, Longman Group: U.K., Ed.: 5, p. 163 (1989).
References
A. Rodríguez, M. Nomen, B.W. Spur and J.J. Godfroid, Tetrahedron Lett., 39, 8563 (1998); https://doi.org/10.1016/S0040-4039(98)01958-3
S. Feng, IOP Conf. Ser.: Earth Environ. Sci., 440, 022019 (2020); https://doi.org/10.1088/1755-1315/440/2/022019
G. Bartoli, J. Boeglin, M. Bosco, M. Locatelli, M. Massaccesi, P. Melchiorre and L. Sambri, Adv. Synth. Catal., 347, 33 (2005); https://doi.org/10.1002/adsc.200404171
T. Mineno and H. Kansui, Chem. Pharm. Bull. (Tokyo), 54, 918 (2006); https://doi.org/10.1248/cpb.54.918
C.S. Cho, D.T. Kim, H.-J. Choi, T.-J. Kim and S.C. Shim, Bull. Korean Chem. Soc., 23, 539 (2002); https://doi.org/10.5012/bkcs.2002.23.4.539
G.-S. Zhang, Synth. Commun., 28, 1159 (1998); https://doi.org/10.1080/00397919808005956
G.V.M. Sharma, A.K. Mahalingam, M. Nagarajan, A. Ilangovan and P. Radhakrishna, Synlett, 1200 (1999); https://doi.org/10.1055/s-1999-2806
R.N. Ram and I. Charles, Tetrahedron, 53, 7335 (1997); https://doi.org/10.1016/S0040-4020(97)00416-X
N. Iranpoor, H. Firouzabadi and M.A. Zolfigol, Synth. Commun., 28, 1923 (1998); https://doi.org/10.1080/00397919808007166
K. Ramalinga, P. Vijayalakshmi and T.N.B. Kaimal, Tetrahedron Lett., 43, 879 (2002); https://doi.org/10.1016/S0040-4039(01)02235-3
B. Neises and W. Steglich, Angew. Chem. Int. Ed. Engl., 17, 522 (1978); https://doi.org/10.1002/anie.197805221
K. Saigo, M. Usui, K. Kikuchi, E. Shimada and T. Mukaiyama, Bull. Chem. Soc. Jpn., 50, 1863 (1977); https://doi.org/10.1246/bcsj.50.1863
K. Wakasugi, A. Nakamura, A. Iida, Y. Nishii, N. Nakatani, S. Fukushima and Y. Tanabe, Tetrahedron, 59, 5337 (2003); https://doi.org/10.1016/S0040-4020(03)00734-8
A.R. Sardarian, M. Zandi and S. Motevally, Acta Chim. Slov., 56, 729 (2009).
G. Höfle, W. Steglich and H. Vorbrüggen, Angew. Chem. Int. Ed. Engl., 17, 569 (1978); https://doi.org/10.1002/anie.197805691
T. Sano, K. Ohashi and T. Oriyama, Synthesis, 1141 (1999); https://doi.org/10.1055/s-1999-3521
K.L. Chandra, P. Saravanan, R.K. Singh and V.K. Singh, Tetrahedron, 58, 1369 (2002); https://doi.org/10.1016/S0040-4020(01)01229-7
S.T. Heller, T. Fu and R. Sarpong, Org. Lett., 14, 1970 (2012); https://doi.org/10.1021/ol300339q
A.R. Katritzky, H.-X. Chang and B. Yang, Synthesis, 503 (1995); https://doi.org/10.1055/s-1995-3959
A.R. Katritzky, B. Yang and D. Semenzin, J. Org. Chem., 62, 726 (1997); https://doi.org/10.1021/jo961537r
B. Phungpis and V. Hahnvajanawong, Asian J. Chem., 33, 651 (2021); https://doi.org/10.14233/ajchem.2021.23113
B. Phungpis, V. Hahnvajanawong and P. Theramongkol, Der Pharma Chem., 8, 167 (2016).
B.S. Furniss, A.J. Hannaford, P.W.G. Smith and A.R. Tatchell, Vogel’s Textbook of practical Organic Chemistry, Longman Group: U.K., Ed.: 5, p. 163 (1989).