Domino condensation/aza-Michael/O→N acyl migration of carbodiimides with activated α,β-unsaturated carboxylic acids to form hydantoins

Tetrahedron Letters

Volumn 44, Issue 47, 2003, Pages 8549-8551

  Volonterio, Alessandro ^a   Zanda, Matteo ^b  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

Aza Michael; Carbodiimides; Domino reaction; Hydantoins

Indexed keywords

ASPARTIC ACID; CARBOXYLIC ACID; CYANAMIDE; HYDANTOIN DERIVATIVE; NITROGEN; OXYGEN;

ARTICLE; FLUORINATION; MICHAEL ADDITION; POLYMERIZATION; SYNTHESIS;

EID: 0142200003     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.134     Document Type: Article

References (16)

1. See for example: Zhang W., Lu Y. Org. Lett. 5:2003;2555-2558. and references cited therein.
2. Tietze L.F. Chem. Rev. 96:1996;115-136.
3. For an overview of the field, see: (a) Fluorine-containing Amino Acids: Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, 1995; (b) Sutherland, A.; Willis, C. L. Nat. Prod. Rep. 2000, 621-631.
4. For an overview of the field, see: (a) Fluorine-containing Amino Acids: Synthesis and Properties; Kukhar, V. P., Soloshonok, V. A., Eds.; Wiley: Chichester, 1995; (b) Sutherland, A.; Willis, C. L. Nat. Prod. Rep. 2000, 621-631.
5. Sheehan J.C., Hess G.P. J. Am. Chem. Soc. 77:1955;1067-1068.
6. For a review, see: Klausner Y.S., Bodansky M. Synthesis. 1:1972;453-463.
7. See for example: (a) Kishikawa, K.; Yamamoto, M.; Kohmoto, S.; Yamada, K. J. Org. Chem. 1989, 54, 2428-2432; (b) Kohmoto, S.; Miyaji, Y.; Tsuruoka, M.; Kishikawa, K.; Yamamoto, M.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 2001, 2082-2088; (c) Anglada, J. M.; Campos, T.; Campos, F.; Camps, F. M.; Moreto, J. M.; Pages, L. J. Heterocycl. Chem. 1996, 33, 1259-1270; (d) Hoskins, W. M.; Crout, D. H. G. J. Chem. Soc,. Perkin Trans. 1 1977, 538-544; (e) Bernasconi, S.; Comini, A.; Corbella, A.; Gariboldi, P.; Sisti, M. Synthesis 1980, 385-387; (f) Xi, Z.; Agback, P.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1991, 47, 9675-9690.
8. See for example: (a) Kishikawa, K.; Yamamoto, M.; Kohmoto, S.; Yamada, K. J. Org. Chem. 1989, 54, 2428-2432; (b) Kohmoto, S.; Miyaji, Y.; Tsuruoka, M.; Kishikawa, K.; Yamamoto, M.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 2001, 2082-2088; (c) Anglada, J. M.; Campos, T.; Campos, F.; Camps, F. M.; Moreto, J. M.; Pages, L. J. Heterocycl. Chem. 1996, 33, 1259-1270; (d) Hoskins, W. M.; Crout, D. H. G. J. Chem. Soc,. Perkin Trans. 1 1977, 538-544; (e) Bernasconi, S.; Comini, A.; Corbella, A.; Gariboldi, P.; Sisti, M. Synthesis 1980, 385-387; (f) Xi, Z.; Agback, P.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1991, 47, 9675-9690.
9. See for example: (a) Kishikawa, K.; Yamamoto, M.; Kohmoto, S.; Yamada, K. J. Org. Chem. 1989, 54, 2428-2432; (b) Kohmoto, S.; Miyaji, Y.; Tsuruoka, M.; Kishikawa, K.; Yamamoto, M.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 2001, 2082-2088; (c) Anglada, J. M.; Campos, T.; Campos, F.; Camps, F. M.; Moreto, J. M.; Pages, L. J. Heterocycl. Chem. 1996, 33, 1259-1270; (d) Hoskins, W. M.; Crout, D. H. G. J. Chem. Soc,. Perkin Trans. 1 1977, 538-544; (e) Bernasconi, S.; Comini, A.; Corbella, A.; Gariboldi, P.; Sisti, M. Synthesis 1980, 385-387; (f) Xi, Z.; Agback, P.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1991, 47, 9675-9690.
10. See for example: (a) Kishikawa, K.; Yamamoto, M.; Kohmoto, S.; Yamada, K. J. Org. Chem. 1989, 54, 2428-2432; (b) Kohmoto, S.; Miyaji, Y.; Tsuruoka, M.; Kishikawa, K.; Yamamoto, M.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 2001, 2082-2088; (c) Anglada, J. M.; Campos, T.; Campos, F.; Camps, F. M.; Moreto, J. M.; Pages, L. J. Heterocycl. Chem. 1996, 33, 1259-1270; (d) Hoskins, W. M.; Crout, D. H. G. J. Chem. Soc,. Perkin Trans. 1 1977, 538-544; (e) Bernasconi, S.; Comini, A.; Corbella, A.; Gariboldi, P.; Sisti, M. Synthesis 1980, 385-387; (f) Xi, Z.; Agback, P.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1991, 47, 9675-9690.
11. See for example: (a) Kishikawa, K.; Yamamoto, M.; Kohmoto, S.; Yamada, K. J. Org. Chem. 1989, 54, 2428-2432; (b) Kohmoto, S.; Miyaji, Y.; Tsuruoka, M.; Kishikawa, K.; Yamamoto, M.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 2001, 2082-2088; (c) Anglada, J. M.; Campos, T.; Campos, F.; Camps, F. M.; Moreto, J. M.; Pages, L. J. Heterocycl. Chem. 1996, 33, 1259-1270; (d) Hoskins, W. M.; Crout, D. H. G. J. Chem. Soc,. Perkin Trans. 1 1977, 538-544; (e) Bernasconi, S.; Comini, A.; Corbella, A.; Gariboldi, P.; Sisti, M. Synthesis 1980, 385-387; (f) Xi, Z.; Agback, P.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1991, 47, 9675-9690.
12. See for example: (a) Kishikawa, K.; Yamamoto, M.; Kohmoto, S.; Yamada, K. J. Org. Chem. 1989, 54, 2428-2432; (b) Kohmoto, S.; Miyaji, Y.; Tsuruoka, M.; Kishikawa, K.; Yamamoto, M.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 2001, 2082-2088; (c) Anglada, J. M.; Campos, T.; Campos, F.; Camps, F. M.; Moreto, J. M.; Pages, L. J. Heterocycl. Chem. 1996, 33, 1259-1270; (d) Hoskins, W. M.; Crout, D. H. G. J. Chem. Soc,. Perkin Trans. 1 1977, 538-544; (e) Bernasconi, S.; Comini, A.; Corbella, A.; Gariboldi, P.; Sisti, M. Synthesis 1980, 385-387; (f) Xi, Z.; Agback, P.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1991, 47, 9675-9690.
13. A conceptually related process involving fumaric acid monomethyl ester and several carbodiimides, in the presence of alcohols and amines, was reported to produce rearranged urea products via the intermediates 6 and 7. In that case, the corresponding hydantoins were occasionally observed as minor byproducts. See: Kishikawa, K.; Sankhavasi, W.; Yoshizaki, K.; Kohmoto, S.; Yamamoto, M.; Yamada, K. J. Chem. Soc., Perkin Trans. 1 1994, 1205-1209. No attempts to produce hydantoins and no description of the reaction course in the absence of alcohols or amines were described therein.
14. 2-Imino-oxazolidin-5-ones 7 have been described and isolated: Brady W.T., Owens R.A. J. Org. Chem. 42:1977;3220-3222.
15. The use of a catalytic base (DMAP or sym-collidine) did not improve the outcome of the reactions involving 5d.
16. A sample of diastereomerically pure Z-5a was obtained by flash chromatography (n-Hex/EtOAc 8:2) of the mixture.