One-pot, regioselective synthesis of 1,3,5 trisubstituted hydantoins by domino condensation/aza-Michael/O → acyl migration of asymmetric carbodiimides with α,β-unsaturated carboxylic acids

Letters in Organic Chemistry

Volumn 2, Issue 1, 2005, Pages 44-46

  Volonterio, Alessandro ^a   Zanda, Matteo ^b  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

Aza Michael; Carbodiimides; Domino reaction; Hydantois; Regiochemistry

Indexed keywords

EID: 15444373805     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178053400298     Document Type: Review

References (11)

1. See for example: (a) Vázquez, J.; Royo, M.; Albericio, F. Lett. Org. Chem. 2004, 1, 224-226.
2. (b) Meusel, M.; Ambrozak, A.; Hecker, T. K.; Gütschow, M. J. Org. Chem. 2003, 68, 4684-4692 and references cited therein.
3. Tictze, L. F. Chem. Rev. 1996, 96, 115-136.
4. (a) Volonterio, A.; Zanda, M. Tetrahedron Lett. 2003, 44, 8549-8551.
5. (b) 2-Imino-oxazolidin-5-ones 4 have been described and isolated: Brady, W. T.; Owens, R. A. J. Org. Chem. 1977, 42, 3220-3222.
6. Examples of regioselective reactions exploiting the reactivity of asymmetric carbodiimides: (a) Saito, T.; Tsuda, K.; Saito, Y.; Tetrahedron Lett. 1996, 37, 209-212.
7. (b) Larksarp, C.; Alper, H. J. Org. Chem. 1998, 63, 6229-6233.
8. (c) Heras, M.; Ventura, M.; Linden, A.; Villalgordo, J. M. Tetrahedron 2001, 57, 4371-4388.
9. Palomo, C.; Mestres, R. Synthesis 1981, 373-374.
10. Reactions of 2c carried out in absence of a base produced the corresponding hydantoin in only modest yields.
11. In the case of entries 4,7 the O → N acyl migration of O- acylisoureas 9 (Scheme 3) was competitive with the intramolecular aza-Michael step, leading to the formation of the corresponding N-acyl ureas as major products. The latter compounds are stable and did not convert spontaneously into hydantoins at r.t.. For a detailed study and discussion of the mechanism of the title reaction see Ref. 3a, as well as: Kishikawa, K.; Sankhavasi, W.; Yoshizaki, K.; Kohmoto, S.; Yamamoto, M.; Yamada, K. J. Chem. Soc. Perkin Trans. 1 1994, 1205-1209.