5-Hydroxy-2H-pyrrol-2-ones and not 2-aminofurans are the cycloaddition products between alkyl isocyanides and benzyliden-1,3-diketones

Tetrahedron Letters

Volumn 45, Issue 7, 2004, Pages 1413-1416

  Quai, Monica ^a   Frattini, Sara ^a   Vendrame, Ugo ^a   Mondoni, Maurizio ^a   Dossena, Simona ^a   Cereda, Enzo ^a  

^a Boehringer Ingelheim Italia SpA   (Italy)

Author keywords

Cycloaddition; Diketones; Furans; Isocyanides; Pyrrol 2 ones

Indexed keywords

ALKYL GROUP; BENZYLIDENE DERIVATIVE; CYANIDE; DIKETONE; FURAN DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 1642578970     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.059     Document Type: Article

References (17)

1. Yavari I., Shaabani A., Maghsoodlou M.T. Monatsh. Chem. 128:1997;697.
2. John I.G., Radom L. J. Am. Chem. Soc. 100:1978;3981.
3. Lythgoe D.J., McClenaghan I., Ramsden C.A. J. Heterocycl. Chem. 30:1993;113.
4. Mp 145 °C versus 144-146 °C (lit.); Elemental analysis found: C, 70.30; H, 7.49; N, 4.31 versus C, 76.10; H, 7.40; N, 4.40 (lit.).
5. · ) (100), 216 (62), 215 (88), 214 (67), 188 (34), 145 (89), 98 (80).
6. 3 (Aldrich N. 16474-7).
7. Ito K., Kato H., Saegusa T. J. Org. Chem. 47:1982;743.
8. 4OH-methanol.
9. Crystallographic data (excluding structure factors) for compound 2c , has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 220054. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk ].
10. +·).
11. Padwa A., Dimitroff M., Liu B. Org. Lett. 2:2000;3233.
12. Ito K., Yakushijin K. Heterocycles. 9:1978;1603.
13. Nicolaou K.C., Baran P.S., Zhong Y.L., Fong K.C., Choi H.S. J. Am. Chem. Soc. 124:2002;2190.
14. Frattini S.; Dossena S. Unpublished results.
15. Ciller J.A., Seoane C., Soto J.L. Ann. Chem. 1:1985;51.
16. Procopiou P.A., Highcock R.M. J. Chem. Soc., Perkin Trans. 1. 3:1994;245.
17. Beck J.J., Stermitz F.R. J. Nat. Prod. 58:1995;1047.