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Synthesis of 3-Hexyl-4-cyan-6,7-dimethoxy Isocoumarin
Corresponding Author(s) : Hai Jiao Dong
Asian Journal of Chemistry,
Vol. 26 No. 12 (2014): Vol 26 Issue 12
Abstract
4-(2-Amino-propanamideyl)-3,4,5,6,7,8,9,10-octahydro-5,6,8-trihydroxy-3-methyl-isocoumarin, which was isolated from Flaveria bidentis (L) Kuntze, had herbicidal activity and its structure was modified in this research in order to get the isocoumarin compouds with higher herbicidal activity. The reaction starts with 2-amino-4,5-dimethoxy benzoate and then diazo iodination, esterfication, heck coupling, cyclization reaction and cyna substitution reaction were tested to obtain 3-hexyl-4-cyan-6,7-dimethoxy isocoumarin. The isocoumarin derivative is an appropriate precursor for the synthesis of new herbicide.
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- J. Arunpanichlert, V. Rukachaisirikul, Y. Sukpondma, S. Phongpaichit, S. Tewtrakul, N. Rungjindamai and J. Sakayaroj, Chem. Pharm. Bull. (Tokyo), 58, 1033 (2010); doi:10.1248/cpb.58.1033.
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- R.M. Heisey and A.R. Ptltnaln, Weed Physiol., 1, 131 (1985).
- T.J. Haig, T.J. Haig, A.N. Seal, J.E. Pratley, M. An and H. Wu, J. Chem. Ecol., 35, 1129 (2009); doi:10.1007/s10886-009-9689-2.
- S. Atta, A. Jana, R. Ananthakirshnan and P.S. Narayana Dhuleep, J. Agric. Food Chem., 58, 11844 (2010); doi:10.1021/jf1027763.
- P. Apostolakos, P. Livanos and B. Galatis, Cell Motil. Cytoskeleton, 66, 342 (2009); doi:10.1002/cm.20366.
- S. Roy, S. Roy, B. Neuenswander, D. Hill and R.C. Larock, J. Comb. Chem., 11, 1128 (2009); doi:10.1021/cc9001197.
- T.L. Yao and R.C. Larock, Tetrahedron Lett., 43, 7401 (2002); doi:10.1016/S0040-4039(02)01731-8.
- R. Rossi, A. Carpita, F. Bellina, P. Stabile and L. Mannina, Tetrahedron, 59, 2067 (2003); doi:10.1016/S0040-4020(03)00212-6.
- H.Y. Liao and C.H. Cheng, J. Org. Chem., 60, 3711 (1995); doi:10.1021/jo00117a023.
- J.H. Hall and M. Gisler, J. Org. Chem., 41, 3769 (1976); doi:10.1021/jo00885a032.
References
J. Arunpanichlert, V. Rukachaisirikul, Y. Sukpondma, S. Phongpaichit, S. Tewtrakul, N. Rungjindamai and J. Sakayaroj, Chem. Pharm. Bull. (Tokyo), 58, 1033 (2010); doi:10.1248/cpb.58.1033.
M. Deshmukh, P. Pawar, M. Joseph, U. Phalgune, R. Kashakar and N.R. Deshpande, Indian J. Exp. Biol., 46, 788 (2008).
R.M. Heisey and A.R. Ptltnaln, Weed Physiol., 1, 131 (1985).
T.J. Haig, T.J. Haig, A.N. Seal, J.E. Pratley, M. An and H. Wu, J. Chem. Ecol., 35, 1129 (2009); doi:10.1007/s10886-009-9689-2.
S. Atta, A. Jana, R. Ananthakirshnan and P.S. Narayana Dhuleep, J. Agric. Food Chem., 58, 11844 (2010); doi:10.1021/jf1027763.
P. Apostolakos, P. Livanos and B. Galatis, Cell Motil. Cytoskeleton, 66, 342 (2009); doi:10.1002/cm.20366.
S. Roy, S. Roy, B. Neuenswander, D. Hill and R.C. Larock, J. Comb. Chem., 11, 1128 (2009); doi:10.1021/cc9001197.
T.L. Yao and R.C. Larock, Tetrahedron Lett., 43, 7401 (2002); doi:10.1016/S0040-4039(02)01731-8.
R. Rossi, A. Carpita, F. Bellina, P. Stabile and L. Mannina, Tetrahedron, 59, 2067 (2003); doi:10.1016/S0040-4020(03)00212-6.
H.Y. Liao and C.H. Cheng, J. Org. Chem., 60, 3711 (1995); doi:10.1021/jo00117a023.
J.H. Hall and M. Gisler, J. Org. Chem., 41, 3769 (1976); doi:10.1021/jo00885a032.