Three-Component Mannich-like Reaction of 2-Aminoimidazole
Sudhir R. Shengule A and Peter Karuso A B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry and Biomolecular Sciences, Macquarie University, NSW 2109, Australia.
B Corresponding author. Email: peter.karuso@mq.edu.au
Australian Journal of Chemistry 64(12) 1617-1620 https://doi.org/10.1071/CH11358
Submitted: 1 September 2011 Accepted: 13 October 2011 Published: 23 November 2011
Abstract
A three-component reaction of 2-aminoimidazole with various aldehydes and amines is described that generates 4-substituted 2-aminoimidazoles containing a new chiral centre, a new C–C bond and a new C–N bond. The reactions can be conducted in water and require only sodium carbonate as reagent.
References
[1] D. J. Newman, M. Cragg, J. Nat. Prod. 2007, 70, 461.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhvFKrsro%3D&md5=51dde6aa79127f4f6ca887dfce8266ecCAS |
[2] R. Breinbauer, I. R. Vetter, H. Waldmann, Angew. Chem. Int. Ed. Engl. 2002, 41, 2878.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmslSrsLk%3D&md5=54354a0d4982d00108fe87fb2cd023d2CAS |
[3] A. Ulaczyk-Lesanko, D. G. Hall, Curr. Opin. Chem. Biol. 2005, 9, 266.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltVaqt78%3D&md5=a97004af906b951fe0918b7bf4497874CAS |
[4] G. Cimino, S. De Stefano, L. Minale, Comp. Biochem. Physiol. 1974, 47B, 895.
[5] A. A. Mourabit, P. Potier, Eur. J. Org. Chem. 2001, 237.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXovVanuw%3D%3D&md5=1662de16429f8dca3662d03d3f8d0f98CAS |
[6] R. B. Kinnel, H. P. Gehrken, R. Swali, G. Skoropowski, P. J. Scheuer, J. Org. Chem. 1998, 63, 3281.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXislGnu74%3D&md5=457e372cd6ce16bc568fdf35ce101c8cCAS |
[7] M. Fujita, Y. Nakao, S. Matsunaga, M. Seiki, Y. Itoh, J. Yamashita, R. W. M. Van Soest, N. Fusetani, J. Am. Chem. Soc. 2003, 125, 15700.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXptlOmu7g%3D&md5=1ac631d6edb9a228229a753419658463CAS |
[8] S. R. Shengule, P. Karuso, Org. Lett. 2006, 8, 4083.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XnsF2gtbw%3D&md5=58bc07e1e5b1aaef5b37272e5cc39beaCAS |
[9] I. Ugi, A. Dömling, W. Hörl, Endeavour 1994, 18, 115.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXis1yltr8%3D&md5=5c9e89903ad07e132428fef968008f7fCAS |
[10] T. Kato, T. Morikawa, Y. Suzuki, Yakugaku Zasshi 1952, 72, 1177.
| 1:CAS:528:DyaG3sXksVChtg%3D%3D&md5=317916ed16ddb672f1ae1ddfb550d52eCAS |
[11] F. B. Stocker, J. L. Kurtz, B. L. Gilman, D. A. Forsyth, J. Org. Chem. 1970, 35, 883.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3cXht1Wnsbo%3D&md5=7abc09f8b366d021d9fc5308cfa26af2CAS |
[12] L. S. Povarov, Russ. Chem. Rev. 1967, 36, 656.
