Preparation of Substituted Imidazolidinones and Hydantoins by Ring-Expansion of Aziridinones

Synlett

Volumn 1997, Issue 6, 1997, Pages 683-684

  Talaty, Erach R ^a   Yusoff, Mashitah M ^a   Ismail, S Asmah ^a   Gomez, Jaime A ^a   Keller, Charles E ^a   Younger, Jean M ^a  

^a WICHITA STATE UNIVERSITY   (United States)

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Indexed keywords

EID: 0002556502     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3256     Document Type: Article

References (13)

1. Lengyel, I.; Sheehan, J.C. Angew. Chem. Int. Ed. Engl. 1968, 25.
2. L'abbe, G. Angew. Chem. Int. Ed. Engl. 1980, 276.
3. Talaty, E.R.; Dupuy, A.E., Jr.; Utermoehlen, C.M. J. Chem. Soc., Chem. Commun. 1971, 16.
4. -1.
5. Matsumoto, K.; Rapoport, H. J. Org. Chem. 1968, 33, 552; Barker, P.L.; Gendler, P.L.; Rapoport, H. J. Org. Chem. 1981, 46, 2455.
6. Matsumoto, K.; Rapoport, H. J. Org. Chem. 1968, 33, 552; Barker, P.L.; Gendler, P.L.; Rapoport, H. J. Org. Chem. 1981, 46, 2455.
7. Kenyon, G.L.; Rowley, G.L. J. Am. Chem. Soc. 1971, 93, 5552.
8. Courtesy of Dr. Mark J. Kurth, University of California, Davis.
9. Work done in conjunction with Dr. Joseph H. Reibenspies, Texas A & M University (to be published).
10. 2Ph).
11. 3) δ 27.1 (q), 28.8 (q), 33.4 (s), 42.8 (t), 50.6 (s), 65.2 (d), 126.9 (d), 127.6 (d), 128.2 (d), 138.4 (s), 174.7 (s).
12. 3OH constitutes a convenient method for determining the mode of ring-opening of 1a by such nucleophiles.
13. For example, the range of the signals for the methyl carbons of the two tert-Bu groups and the α-carbon in the common piece of the structure [t-BuNH-CH(t-Bu)-CO] are δ 27.1-27.4 (q), 28.5-29.0 (q) and 65.2-66.1 (d), respectively.