Oxidative Dimerisation of Isoflavones: Synthesis of Kudzuisoflavone A and Related Compounds*
Mandar Deodhar A , Kasey Wood A , David StClair Black A and Naresh Kumar A B
+ Author Affiliations
- Author Affiliations
A School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia.
B Corresponding author. Email: n.kumar@unsw.edu.au
Australian Journal of Chemistry 65(10) 1377-1383 https://doi.org/10.1071/CH12108
Submitted: 20 February 2012 Accepted: 12 April 2012 Published: 20 June 2012
Abstract
Kudzuisoflavone-A was successfully synthesised via oxidative dimerisation of daidzein in the presence of cuprous chloride. Appropriately substituted isoflavones also undergo regioselective oxidative dimerisation when treated with thallium trifluoroacetate to give novel 6′,6′″-biisoflavones in good yield. A rationale for the regioselectivity is proposed.
References
[1] M. Duenas, T. Hernandez, I. Estrella, R. Rabanal, Food Chem. 2003, 82, 373.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXksFKksbs%3D&md5=7e7013eac27e7411dc9693ff07064420CAS |
[2] N. Kumar, A. Heaton, Chem. Abstr. 2002, 137, 232488.
[3] A. Ogundaini, M. Farah, P. Perera, G. Samuelsson, L. Bohlin, J. Nat. Prod. 1996, 59, 587.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xjt1Kgsr8%3D&md5=363f0d71a4787d870a15f2f7dcfc69c5CAS |
[4] Y. M. Lin, D. E. Zembower, M. T. Flavin, R. Schure, G. U. S. Zhao, Patent 6399654, 2002.
[5] U. Sankawa, T. Hakamatsuka, K. Shinkai, M. Yoshida, H.-H. Park, Y. Ebizuka, Curr. Plant Sci. Biotechnol. Agric. 1995, 22, 595.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXmvFCisb4%3D&md5=fcbbf3ac4307efd383e34d4f539781d0CAS |
[6] M. Sugano, Y. Ogura, E. Hoshino, T. Hamada, R. Enokida, Y. Takamatsu, Chem. Abstr. 1997, 126, 276427.
[7] Oxidative Coupling of Phenols (Eds W. I. Taylor, A. R. Battersby) 1967, Vol. 1 (Dekker: New York, NY).
[8] S. Tobinaga, E. Kotani, J. Am. Chem. Soc. 1972, 94, 309.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE38Xnt1WmsA%3D%3D&md5=1aa88b0fcdb44d14c84506b937ba0ab7CAS |
[9] T. C. Jempty, L. L. Miller, J. Org. Chem. 1980, 45, 749.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXhtFSjt7g%3D&md5=28a2ce0912082830a1414a8a4e2a2f91CAS |
[10] M. Nakajima, I. Miyoshi, K. Kanayama, S. I. Hashimoto, M. Noji, K. Koga, J. Org. Chem. 1999, 64, 2264.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhs1elt7w%3D&md5=a31f481c05e00fba2038a2e4fec340bbCAS |
[11] R. Pummerer, D. Melamed, H. Puttfarcken, Ber. Dtsch. Chem. Ges. 1922, 55B, 3116.
| 1:CAS:528:DyaB3sXktFSj&md5=4ab2f501465aad6d0edb3690ce0be66fCAS |
[12] K. Chakrabarty, H. M. Chawla, V. V. Suresh, Indian J. Chem. B 1992, 31B, 464.
| 1:CAS:528:DyaK38XlsFSlsb4%3D&md5=510c388392a38c4cc2feb16b3edad91bCAS |
[13] T. Pal, A. Pal, J. Indian Chem. Soc. 1990, 67, 387.
| 1:CAS:528:DyaK3MXkt1WlsA%3D%3D&md5=9fa3d32b3732a03d664341740ca5de10CAS |
[14] W. L. Carrick, G. L. Karapinka, G. T. Kwiatkowski, J. Org. Chem. 1969, 34, 2388.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1MXkslShsLg%3D&md5=5265200ffc1b550a7e329d0ee6dc62beCAS |
[15] A. S. Kende, L. S. Liebeskind, J. Am. Chem. Soc. 1976, 98, 267.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE28XptVSntw%3D%3D&md5=759270312b10b5278fa2ad9ed61d83a4CAS |
[16] R. E. Damon, R. H. Schlessinger, J. F. Blount, J. Org. Chem. 1976, 41, 3772.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE28XlvFalsr0%3D&md5=76ad78009c06751af355dc1577313dc2CAS |
[17] A. G. Brown, P. D. Edwards, Tetrahedron Lett. 1990, 31, 6581.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXht1ejsLc%3D&md5=c3a5185031befe505b3bf464e210f720CAS |
[18] S. M. Kupchan, A. J. Liepa, V. Kameswaran, R. F. Bryan, J. Am. Chem. Soc. 1973, 95, 6861.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2cXjs1yi&md5=85d7696a0bdf9cfb2f44ab88265aac0fCAS |
[19] M. J. S. Dewar, T. Nakaya, J. Am. Chem. Soc. 1968, 90, 7134.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1MXkslSjsA%3D%3D&md5=7dc39f2b1d9e1293d040a35381fdf771CAS |
[20] A. McKillop, A. G. Turrell, D. W. Young, E. C. Taylor, J. Am. Chem. Soc. 1980, 102, 6504.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXmt1Snu7Y%3D&md5=b8a89586ce5c54200424e8d096c3abd4CAS |
[21] E. C. Taylor, J. G. Andrade, G. J. H. Rall, A. McKillop, J. Am. Chem. Soc. 1980, 102, 6513.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXmt1Sqt7o%3D&md5=92a48e1f419b07f1938f5e391487381cCAS |
[22] R. O. C. Norman, C. B. Thomas, J. S. Willson, J. Chem. Soc., Perkin Trans. 1 1973, 325.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3sXotl2iug%3D%3D&md5=db4047de5e1a8e81734aa2e816756374CAS |
[23] G. Bringmann, S. Tasler, H. Endress, J. Kraus, K. Messer, M. Wohlfarth, W. Lobin, J. Am. Chem. Soc. 2001, 123, 2703.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXhsVKmsrc%3D&md5=dc97930aad282357c429ce8eb56ddd36CAS |
[24] M. Deodhar, D. StC. Black, N. Kumar, Org. Prep. Proced. Int. 2006, 38, 94.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhslCltLc%3D&md5=5a566e6a0ecb902ed1555a82547dfa03CAS |
[25] M. Deodhar, D. StC. Black, N. Kumar, Tetrahedron 2007, 63, 5227.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXlt1GqurY%3D&md5=00d34430becc49835d0615e7d9df3e3fCAS |
[26] M. Deodhar, D. StC. Black, D. S.-H. Chan, N. Kumar, Heterocycles 2010, 80, 1267.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXjs1KrtrY%3D&md5=bc4c79e08b1c4fc244239df72d04693bCAS |
[27] M. Deodhar, D. StC. Black, D. S.-H. Chan, N. Kumar, Heterocycles 2011, 82, 1489.
| 1:CAS:528:DC%2BC3MXjslGqs74%3D&md5=d565d7cb1dcc4183148edee17b3b1d59CAS |
[28] G. Sartori, R. Maggi, F. Bigi, A. Arienti, G. Casnati, Tetrahedron Lett. 1992, 33, 2207.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38Xkt1Gqu7Y%3D&md5=421fbb091a2e8b690531731a794836e0CAS |
[29] F. Toda, K. Tanaka, S. Iwata, J. Org. Chem. 1989, 54, 3007.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXkslOls78%3D&md5=5771c938b0cf5826f7d0ee6ff55f7f80CAS |
[30] K. V. Rama Krishna, K. Sujatha, R. S. Kapil, Tetrahedron Lett. 1990, 31, 1351.
| Crossref | GoogleScholarGoogle Scholar |
[31] M. Smrcina, M. Lorenc, V. Hanus, P. Kocovsky, Synlett 1991, 231.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXkt1yrtr4%3D&md5=9084e0a55a045f75609cfedbf26d5bb3CAS |
[32] K. Omura, J. Org. Chem. 1984, 49, 3046.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXkvFSmsro%3D&md5=71204d09f492e75fe9f109f8870b0386CAS |
[33] R. Jiang, B. Li, C. Xiao, D. Yang, J. Wu, Zhongguo Kangshengsu Zazhi 1997, 22, 81.
| 1:CAS:528:DyaK2sXmvVemu7g%3D&md5=fe263cdbb5b4bffd015962d827336902CAS |
[34] R. Ueno, M. Kitayama, K. Minami, H. Wakamori, H. Hirai, Chem. Abstr. 2002, 137, 337681.
[35] G. B. Deacon, R. N. M. Smith, J. Fluor. Chem. 1980, 15, 85.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXhvVWht74%3D&md5=2d280d387afe84b54249efc54b8721ebCAS |
[36] B. Dansou, C. Pichon, R. Dhal, E. Brown, S. Mille, Eur. J. Org. Chem. 2000, 1527.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjtVeit7o%3D&md5=7cc998d2ccbb0dfda5a0dc5b23e6c2acCAS |
[37] M. L. dos Santos, G. C. de Magalhaes, R. Braz Filho, J. Organomet. Chem. 1996, 526, 15.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXltVCquw%3D%3D&md5=1857f98f87be495cfc660379a887fa8fCAS |
[38] T. Hakamatsuka, K. Shinkai, H. Noguchi, Y. Ebizuka, U. Sankawa, Z. Naturforsch. C 1992, 47, 177.
| 1:CAS:528:DyaK38XksVCmtbk%3D&md5=966be199af6e68a06b19a1bf5db58442CAS |
[39] M. Shamma, L. D. Stiver, Tetrahedron 1969, 25, 3887.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1MXltVWlt78%3D&md5=f5670dd3b6fca2e3420fd1fd851e5f10CAS |
[40] L. Farkas, A. Major, L. Pallos, J. Varady, Chem. Ber. 1958, 91, 2858.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1MXksFWrsQ%3D%3D&md5=3c46e0dc290f49c76b048ef0c8d9342eCAS |
[41] C. A. K. Gray, P. T. Kaye, A. T. Nchinda, J. Nat. Prod. 2003, 66, 1144.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXlvFaktrw%3D&md5=00d4027562c4d99c4bb97fd00d073b8dCAS |
[42] H.-W. Chu, H.-T. Wu, Y.-J. Lee, Tetrahedron 2004, 60, 2647.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhsFeqsLg%3D&md5=3a1f22a91256f648446b951df2831d95CAS |
[43] G. Lindberg, B.-G. Osterdahl, E. Nilsson, Chem. Scr. 1974, 5, 140.
| 1:CAS:528:DyaE2cXltVWrs70%3D&md5=65814338d7b28f3ac4b665d22e9d2db7CAS |
