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

Author:

Alves Maria José,Ferreira Paula M.T,Maia Hernâni L.S,Monteiro Luı́s S,Gilchrist Thomas L

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference11 articles.

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. General procedure for preparation of aziridines 3: The appropriate heterocycle (1 mmol) was added to a rapidly stirred solution of the azirine 1 (1 mmol) in acetonitrile (10 mL) at room temperature containing a suspension of K2CO3 (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.

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