Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Reactions of Huisgen Zwitterions with Diphenyl Cyclopropenone: A Novel Strategy for the Synthesis of Oxazinone Derivatives
Corresponding Author(s) : R. Divya Mohan
Asian Journal of Chemistry,
Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018
Abstract
A facile and novel route for the synthesis of diphenyl oxazinones in good yield was developed using diphenyl cyclopropenone and dialkyl azodicarboxylate with triphenyl phosphine as catalyst at room temperature and are well characterized using spectroscopic studies.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen and L. Balagopal, Acc. Chem. Res., 36, 899 (2003); https://doi.org/10.1021/ar020258p.
- V. Nair, R.S. Menon, A.R. Sreekanth, N. Abhilash and A.T. Biju, Acc. Chem. Res., 39, 520 (2006); https://doi.org/10.1021/ar0502026.
- Y.-L. Shi, and M. Shi, Org. Lett., 7, 3057 (2005); https://doi.org/10.1021/ol051044l.
- D.W. Allen, Organophosphorus Chem., 44, 1 (2015); https://doi.org10.1039/9781782622765-00001.
- R. Huisgen, E. Brunn, R. Gilardi and I. Karle, J. Am. Chem. Soc., 91, 7766 (1969); https://doi.org/10.1021/ja50001a054.
- P. Narender, U. Srinivas, M. Ravinder, B.A. Rao, K. Harakishore, C. Ramesh, B.S. Gangadasu, N. Murthy and V.J. Rao, Biorg. Med. Chem., 14, 4600 (2006); https://doi.org/10.1016/j.bmc.2006.02.020.
- M. Girard, P. Murphy and N. Tsou, Tetrahedron Lett., 46, 2449 (2005); https://doi.org/10.1016/j.tetlet.2005.02.051.
- M. Marigo, K. Juhl and K.A. Jørgensen, Angew. Chem. Int. Ed., 42, 1367 (2003); https://doi.org/10.1002/anie.200390350.
- R. Breslow, T. Eicher, A. Krebs, R.A. Peterson and J. Posner, J. Am. Chem. Soc., 87, 1323 (1965); https://doi.org/10.1021/ja01084a029.
- C.W. Bird and A.F. Hamer, Org. Prepn. Proc., 2, 79 (1970); https://doi.org/10.1080/00304947009458607.
- S.W. Tobey and R. West, J. Am. Chem. Soc., 86, 4215 (1964); https://doi.org/10.1021/ja01073a075.
- J.E. Marino and A. Resendiz, Org. Lett., 7, 371 (2005); https://doi.org/10.1021/ol0480527.
- S. Saaby, M.A. Bella and K.A. Jørgensen, J. Am. Chem. Soc., 126, 8120 (2004); https://doi.org/10.1021/ja047704j.
- A.S. Hossan, H.M. Abu-Melha and M.A. Al-Omar, Molecules, 17, 11 (2012); https://doi.org/10.3390/molecules171113642
References
V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen and L. Balagopal, Acc. Chem. Res., 36, 899 (2003); https://doi.org/10.1021/ar020258p.
V. Nair, R.S. Menon, A.R. Sreekanth, N. Abhilash and A.T. Biju, Acc. Chem. Res., 39, 520 (2006); https://doi.org/10.1021/ar0502026.
Y.-L. Shi, and M. Shi, Org. Lett., 7, 3057 (2005); https://doi.org/10.1021/ol051044l.
D.W. Allen, Organophosphorus Chem., 44, 1 (2015); https://doi.org10.1039/9781782622765-00001.
R. Huisgen, E. Brunn, R. Gilardi and I. Karle, J. Am. Chem. Soc., 91, 7766 (1969); https://doi.org/10.1021/ja50001a054.
P. Narender, U. Srinivas, M. Ravinder, B.A. Rao, K. Harakishore, C. Ramesh, B.S. Gangadasu, N. Murthy and V.J. Rao, Biorg. Med. Chem., 14, 4600 (2006); https://doi.org/10.1016/j.bmc.2006.02.020.
M. Girard, P. Murphy and N. Tsou, Tetrahedron Lett., 46, 2449 (2005); https://doi.org/10.1016/j.tetlet.2005.02.051.
M. Marigo, K. Juhl and K.A. Jørgensen, Angew. Chem. Int. Ed., 42, 1367 (2003); https://doi.org/10.1002/anie.200390350.
R. Breslow, T. Eicher, A. Krebs, R.A. Peterson and J. Posner, J. Am. Chem. Soc., 87, 1323 (1965); https://doi.org/10.1021/ja01084a029.
C.W. Bird and A.F. Hamer, Org. Prepn. Proc., 2, 79 (1970); https://doi.org/10.1080/00304947009458607.
S.W. Tobey and R. West, J. Am. Chem. Soc., 86, 4215 (1964); https://doi.org/10.1021/ja01073a075.
J.E. Marino and A. Resendiz, Org. Lett., 7, 371 (2005); https://doi.org/10.1021/ol0480527.
S. Saaby, M.A. Bella and K.A. Jørgensen, J. Am. Chem. Soc., 126, 8120 (2004); https://doi.org/10.1021/ja047704j.
A.S. Hossan, H.M. Abu-Melha and M.A. Al-Omar, Molecules, 17, 11 (2012); https://doi.org/10.3390/molecules171113642