Novel aziridine esters by the addition of aromatic nitrogen heterocycles to a 2H-azirine-3-carboxylic ester

Tetrahedron Letters

Volumn 41, Issue 25, 2000, Pages 4991-4995

  Alves, Maria José ^a   Ferreira, Paula M T ^a   Maia, Hernâni L S ^a   Monteiro, Luís S ^a   Gilchrist, Thomas L ^b  

^a UNIVERSITY OF MINHO   (Portugal)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

2H azirines; 5H pyrrolo 1,2 c imidazoles; Aziridines

Indexed keywords

AZIRIDINE DERIVATIVE; BENZALDEHYDE DERIVATIVE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; NITROGEN DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0034686275     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00755-3     Document Type: Article

References (14)

1. Backes, J. Methoden der Organischen Chemie (Houben-Weyl); Klamann, D., Ed.; Georg Thieme Verlag: Stuttgart, 1992; Vol. E16c, pp. 317-369.
2. Alves, M. J.; Gilchrist, T. L.; Sousa, J. H. J. Chem. Soc., Perkin Trans. 1 1999, 1305-1310.
3. Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 1999, 40, 4099-4102.
4. 3 (6 mmol). The reaction mixture was monitored by TLC until no azirine 1 was detectable. The reaction mixture was then filtered and the filtrate was evaporated to dryness. The residue contained the aziridine 3 by NMR, in some cases together with traces of a diastereoisomer (Table 1). Analytical samples were obtained by crystallisation of the residues; all new compounds gave correct elemental analyses.
5. Barroso, M. T.; Kascheres, A. J. Org. Chem. 1999, 64, 49-53.
6. 3) δ 3.29 (1H, s, aziridine 3-H), 3.6 (1H, br, NH), 6.46 (1H, t, J=2.1 Hz, pyrazole 4-H), 7.25-7.35 (3H, m, Ar-H), 7.34 (1H, dd, J=2.0 and 0.5 Hz, 5-H) and 7.92 (1H, dd, J=2.0 and 0.5 Hz, 3-H).
7. 3): 52.23, 53.38, 119.64, 120.80, 133.47, 133.68, 145.07 and 159.02. Compounds 5b-5d have analogous spectra.
8. Antonini, I.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Heterocycl. Chem. 1976, 13, 111-112; Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1989, 957-960; McNab, H. J. Chem. Soc., Perkin Trans. 1 1987, 653-656; McNab, H.; Thornley, C. J. Chem. Soc., Perkin Trans. 1 1997, 2203-2209.
9. Antonini, I.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Heterocycl. Chem. 1976, 13, 111-112; Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1989, 957-960; McNab, H. J. Chem. Soc., Perkin Trans. 1 1987, 653-656; McNab, H.; Thornley, C. J. Chem. Soc., Perkin Trans. 1 1997, 2203-2209.
10. Antonini, I.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Heterocycl. Chem. 1976, 13, 111-112; Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1989, 957-960; McNab, H. J. Chem. Soc., Perkin Trans. 1 1987, 653-656; McNab, H.; Thornley, C. J. Chem. Soc., Perkin Trans. 1 1997, 2203-2209.
11. Antonini, I.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Heterocycl. Chem. 1976, 13, 111-112; Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1989, 957-960; McNab, H. J. Chem. Soc., Perkin Trans. 1 1987, 653-656; McNab, H.; Thornley, C. J. Chem. Soc., Perkin Trans. 1 1997, 2203-2209.
12. 3) 2.35 (3H, s, 1-Me), 3.87 (2H, s, 9-H), 4.02 (3H, s, ester Me), 7.30 (1H, td, J=7.8 and 0.9 Hz), 7.40 (1H, t, J=7.8 Hz), 7.48 (1H, d, J=7.5 Hz) and 8.66 (1H, d, J=7.8 Hz).
13. Alves, M. J.; Gilchrist, T. L. Tetrahedron Lett. 1998, 39, 7579-7582.
14. 3′,NH=11.1 Hz, 3′-H), 7.92 (1H, s) and 8.26 (1H, s).