Copyright (c) 2024 Mrityunjoy Datta
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Synthesis of Linear 6-Allylated-7-hydroxycoumarins: para-Claisen Rearrangement of 2'-Allylated/Prenylated Derivatives of 4'-Prenyloxy Cinnamic Acid
Corresponding Author(s) : Mrityunjoy Datta
Asian Journal of Chemistry,
Vol. 37 No. 1 (2025): Vol 37 Issue 1, 2025
Abstract
Linear 6-allylated-7-hydroxycoumarins were synthesized by the para-Claisen rearrangement of 4'-prenyloxy cinnamic acid derivatives under refluxing condition in N,N-diethylaniline. This method eliminates the requirement for an additional Lewis acid, such as boron trifluoride etherate or trichloride, to convert 7-alkoxycoumarins into 7-hydroxycoumarins, unlike alternative techniques.
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- G.M.D. Forno, E. Latocheski, C.D. Navo, B.L. Albuquerque, A.L. St John, F. Avenier, G. Jimenez-Oses and J.B. Domingos, Chem. Sci., 15, 4458 (2024); https://doi.org/10.1039/D3SC06408E
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- C. Chena, Z.-B. Tang and Z. Liu, Chin. Chem. Lett., 34, 108396 (2023); https://doi.org/10.1016/j.cclet.2023.108396
- A. Roy, A.D. Gupta and K. Sen, Indian J. Chem., 12, 564 (1974).
- N.H. Pardanani and K.N. Trivedi, Aust. J. Chem., 25, 1537 (1972); https://doi.org/10.1071/CH9721537
- J.B. Del Castillo, J.C. U-Rodrignez and F.L. Rodrignez, An. Quim. Sec. C, 81, 106 (1985).
- M. Bandopadhyay, N.P. Pardeshi and T.R. Seshadri, Indian J. Chem., 12, 23 (1974).
- N. Cairns, L.M. Harwood and D.P. Astles, J. Chem. Soc. Chem. Commun., 1264 (1986); https://doi.org/10.1039/c39860001264
- R.S. Mali, P.P. Joshi, P.K. Sandhu and A. Manekar-Tilve, J. Chem. Soc., Perkin Trans. 1, 371 (2002); https://doi.org/10.1039/b109597h
- A. Estévez-Braun and A. G. González, Nat. Prod. Rep., 14, 465 (1997); https://doi.org/10.1039/NP9971400465
- N. Cairns, L.M. Harwood, D.P. Astles and A. Orr, J. Chem. Soc. Chem. Commun., 182 (1986); https://doi.org/10.1039/C39860000182
- N. Cairns, L.M. Harwood and D.P. Astles, J. Chem. Soc. Chem. Commun., 750 (1986); https://doi.org/10.1039/C39860000750
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- B. Chaudhury, S.K. Saha and A. Chatterjee, J. Indian Chem. Soc., 39, 783 (1962).
References
G.M.D. Forno, E. Latocheski, C.D. Navo, B.L. Albuquerque, A.L. St John, F. Avenier, G. Jimenez-Oses and J.B. Domingos, Chem. Sci., 15, 4458 (2024); https://doi.org/10.1039/D3SC06408E
S. Yadav, S. Singh and C. Gupta, Curr. Res. Green Sustain. Chem., 5, 100260 (2022); https://doi.org/10.1016/j.crgsc.2022.100260
S.K. Samanta, S.Patra, B. Biswas, A.H. Patra, P. Ghosh, T. Mistri, D. Rout and P. Patra, Monatsh. Chem., 155, 997 (2024); https://doi.org/10.1007/s00706-024-03252-x
C. Chena, Z.-B. Tang and Z. Liu, Chin. Chem. Lett., 34, 108396 (2023); https://doi.org/10.1016/j.cclet.2023.108396
A. Roy, A.D. Gupta and K. Sen, Indian J. Chem., 12, 564 (1974).
N.H. Pardanani and K.N. Trivedi, Aust. J. Chem., 25, 1537 (1972); https://doi.org/10.1071/CH9721537
J.B. Del Castillo, J.C. U-Rodrignez and F.L. Rodrignez, An. Quim. Sec. C, 81, 106 (1985).
M. Bandopadhyay, N.P. Pardeshi and T.R. Seshadri, Indian J. Chem., 12, 23 (1974).
N. Cairns, L.M. Harwood and D.P. Astles, J. Chem. Soc. Chem. Commun., 1264 (1986); https://doi.org/10.1039/c39860001264
R.S. Mali, P.P. Joshi, P.K. Sandhu and A. Manekar-Tilve, J. Chem. Soc., Perkin Trans. 1, 371 (2002); https://doi.org/10.1039/b109597h
A. Estévez-Braun and A. G. González, Nat. Prod. Rep., 14, 465 (1997); https://doi.org/10.1039/NP9971400465
N. Cairns, L.M. Harwood, D.P. Astles and A. Orr, J. Chem. Soc. Chem. Commun., 182 (1986); https://doi.org/10.1039/C39860000182
N. Cairns, L.M. Harwood and D.P. Astles, J. Chem. Soc. Chem. Commun., 750 (1986); https://doi.org/10.1039/C39860000750
R.D.H. Murray, M.M. Ballantyne and K.P. Mathai, Tetrahedron, 27, 1247 (1971); https://doi.org/10.1016/S0040-4020(01)90873-7
B. Chaudhury, S.K. Saha and A. Chatterjee, J. Indian Chem. Soc., 39, 783 (1962).