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Plausible Reaction Path for Haval-Argade Contrathermodynamic Rearrangement in Synthesis of Farinomalein
Corresponding Author(s) : Narayan P. Firke
Asian Journal of Chemistry,
Vol. 30 No. 4 (2018): Vol 30 Issue 4
Abstract
This work reports, the plausible reaction path in context of the farinomalein (1) and isofarinomalein (2) synthesized via Stobbe condensation and Haval-Argade Contrathermodynamic Rearrangement.
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- S.P. Putri, H. Kinoshita, F. Ihara, Y. Igarashi and T. Nihira, J. Nat. Prod., 72, 1544 (2009); https://doi.org/10.1021/np9002806.
- AI. Molnar, D.M. Gibsonc and S.B. Krasnoffc, Nat. Prod. Rep., 27, 1241 (2010); https://doi.org/10.1039/C001459C.
- R.A. Davis, A.R. Carroll, K.T. Andrews, G.M. Boyle, T.L. Tran, P.C. Healy, J.A. Kalaitzisc and R.G. Shivasd, Org. Biomol. Chem., 8, 1785 (2010); https://doi.org/10.1039/B924169H.
- M.E. Amrani, A. Debbab, A.H. Aly, V. Wray, S. Dobretsov, W.E.G. Maller, W. Lin, D. Lai and P. Proksch, Tetrahedron Lett., 53, 6721 (2012); https://doi.org/10.1016/j.tetlet.2012.10.011.
- W.H. Miles and M. Yan, Tetrahedron Lett., 51, 1710 (2010); https://doi.org/10.1016/j.tetlet.2010.01.083.
- S.T. Aiwale, P. Sardi and S. Dallavalle, Synth. Commun., 43, 1455 (2012); https://doi.org/10.1080/00397911.2011.640969.
- S. Lahore, S.T. Aiwale, P. Sardi and S. Dallavalle, Tetrahedron Lett., 55, 4196 (2014); https://doi.org/10.1016/j.tetlet.2014.05.023.
- K. Tanaka, T. Sugino and F. Toda, Green Chem., 2, 303 (2000); https://doi.org/10.1039/B006565J.
- J.D. White, P. Hrnciar and F. Stappenbeck, J. Org. Chem., 64, 7871 (1999); https://doi.org/10.1021/jo990905z.
- K.P. Haval and N.P. Argade, Tetrahedron, 62, 3557 (2006); https://doi.org/10.1016/j.tet.2006.01.091.
- Y. Furuya, K. Ishihara and H. Yamamoto, J. Am. Chem. Soc., 127, 11240 (2005); https://doi.org/10.1021/ja053441x.
- K.P. Haval, S.B. Mhaske and N.P. Argade, Tetrahedron, 62, 937 (2006); https://doi.org/10.1016/j.tet.2005.10.027.
- J.E. Baldwin and M.J. Lusch, Tetrahedron, 38, 2939 (1982); https://doi.org/10.1016/0040-4020(82)85023-0.
- J.E. Baldwin and L.I. Kruse, J. Chem. Soc., Chem. Commun., 233 (1977); https://doi.org/10.1039/C39770000233.
- M.B. Smith and J. March, March’s Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Wiley-Interscience, USA, p. 323 (2007).
References
S.P. Putri, H. Kinoshita, F. Ihara, Y. Igarashi and T. Nihira, J. Nat. Prod., 72, 1544 (2009); https://doi.org/10.1021/np9002806.
AI. Molnar, D.M. Gibsonc and S.B. Krasnoffc, Nat. Prod. Rep., 27, 1241 (2010); https://doi.org/10.1039/C001459C.
R.A. Davis, A.R. Carroll, K.T. Andrews, G.M. Boyle, T.L. Tran, P.C. Healy, J.A. Kalaitzisc and R.G. Shivasd, Org. Biomol. Chem., 8, 1785 (2010); https://doi.org/10.1039/B924169H.
M.E. Amrani, A. Debbab, A.H. Aly, V. Wray, S. Dobretsov, W.E.G. Maller, W. Lin, D. Lai and P. Proksch, Tetrahedron Lett., 53, 6721 (2012); https://doi.org/10.1016/j.tetlet.2012.10.011.
W.H. Miles and M. Yan, Tetrahedron Lett., 51, 1710 (2010); https://doi.org/10.1016/j.tetlet.2010.01.083.
S.T. Aiwale, P. Sardi and S. Dallavalle, Synth. Commun., 43, 1455 (2012); https://doi.org/10.1080/00397911.2011.640969.
S. Lahore, S.T. Aiwale, P. Sardi and S. Dallavalle, Tetrahedron Lett., 55, 4196 (2014); https://doi.org/10.1016/j.tetlet.2014.05.023.
K. Tanaka, T. Sugino and F. Toda, Green Chem., 2, 303 (2000); https://doi.org/10.1039/B006565J.
J.D. White, P. Hrnciar and F. Stappenbeck, J. Org. Chem., 64, 7871 (1999); https://doi.org/10.1021/jo990905z.
K.P. Haval and N.P. Argade, Tetrahedron, 62, 3557 (2006); https://doi.org/10.1016/j.tet.2006.01.091.
Y. Furuya, K. Ishihara and H. Yamamoto, J. Am. Chem. Soc., 127, 11240 (2005); https://doi.org/10.1021/ja053441x.
K.P. Haval, S.B. Mhaske and N.P. Argade, Tetrahedron, 62, 937 (2006); https://doi.org/10.1016/j.tet.2005.10.027.
J.E. Baldwin and M.J. Lusch, Tetrahedron, 38, 2939 (1982); https://doi.org/10.1016/0040-4020(82)85023-0.
J.E. Baldwin and L.I. Kruse, J. Chem. Soc., Chem. Commun., 233 (1977); https://doi.org/10.1039/C39770000233.
M.B. Smith and J. March, March’s Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Wiley-Interscience, USA, p. 323 (2007).