{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,5]],"date-time":"2026-04-05T05:47:22Z","timestamp":1775368042009,"version":"3.50.1"},"reference-count":11,"publisher":"Elsevier BV","issue":"25","license":[{"start":{"date-parts":[[2000,6,1]],"date-time":"2000-06-01T00:00:00Z","timestamp":959817600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Tetrahedron Letters"],"published-print":{"date-parts":[[2000,6]]},"DOI":"10.1016\/s0040-4039(00)00755-3","type":"journal-article","created":{"date-parts":[[2002,7,25]],"date-time":"2002-07-25T12:00:43Z","timestamp":1027598443000},"page":"4991-4995","source":"Crossref","is-referenced-by-count":15,"title":["Novel aziridine esters by the addition of aromatic nitrogen heterocycles to a 2H-azirine-3-carboxylic ester"],"prefix":"10.1016","volume":"41","author":[{"given":"Maria Jos\u00e9","family":"Alves","sequence":"first","affiliation":[]},{"given":"Paula M.T","family":"Ferreira","sequence":"additional","affiliation":[]},{"given":"Hern\u00e2ni L.S","family":"Maia","sequence":"additional","affiliation":[]},{"given":"Lu\u0131\u0301s S","family":"Monteiro","sequence":"additional","affiliation":[]},{"suffix":"*","given":"Thomas L","family":"Gilchrist","sequence":"additional","affiliation":[]}],"member":"78","reference":[{"key":"10.1016\/S0040-4039(00)00755-3_BIB1","unstructured":"Backes, J. Methoden der Organischen Chemie (Houben\u2013Weyl); Klamann, D., Ed.; Georg Thieme Verlag: Stuttgart, 1992; Vol. E16c, pp. 317\u2013369."},{"key":"10.1016\/S0040-4039(00)00755-3_BIB2","doi-asserted-by":"crossref","unstructured":"Alves, M. J.; Gilchrist, T. L.; Sousa, J. H. J. Chem. Soc., Perkin Trans. 1 1999, 1305\u20131310.","DOI":"10.1039\/a901145e"},{"key":"10.1016\/S0040-4039(00)00755-3_BIB3","doi-asserted-by":"crossref","unstructured":"Ferreira, P. M. T.; Maia, H. L. S.; Monteiro, L. S. Tetrahedron Lett. 1999, 40, 4099\u20134102.","DOI":"10.1016\/S0040-4039(99)00691-7"},{"key":"10.1016\/S0040-4039(00)00755-3_BIB4","unstructured":"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."},{"key":"10.1016\/S0040-4039(00)00755-3_BIB5","doi-asserted-by":"crossref","unstructured":"Barroso, M. T.; Kascheres, A. J. Org. Chem. 1999, 64, 49\u201353.","DOI":"10.1021\/jo980198u"},{"key":"10.1016\/S0040-4039(00)00755-3_BIB6","unstructured":"The acid 4 was isolated (65%) from the hydrolysis of 3b by NaOH in dioxane and had mp 111\u2013112\u00b0C; 1H NMR (300 MHz, CDCl3) \u03b4 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\u20137.35 (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)."},{"key":"10.1016\/S0040-4039(00)00755-3_BIB7","unstructured":"TFA (1 mmol) was added to a rapidly stirred solution of the aziridine 3c (1 mmol) in acetonitrile (10 mL) at room temperature. The course of the reaction was followed by TLC and when no starting material remained the solution was evaporated to dryness under reduced pressure. The crude residue was dissolved in ethyl acetate and, after washing with aq. NaHCO3 and silica gel chromatography, gave the ester 5a (89%), mp 97.5\u201398.5\u00b0C (from ethyl acetate\u2013ether); \u03b4H (300 MHz, CDCl3): \u03b4 3.97 (3H, s, Me), 4.78 (2H, t, J56=J57=1.8 Hz, 5-H), 6.57 (1H, dt, J67=6.1 Hz, J56=1.8 Hz, 6-H), 6.69 (1H, dt, J67=6.1 Hz, J57=1.8 Hz, 7-H) and 7.05 (1H, s, 1-H); \u03b4C (75 MHz, CDCl3): 52.23, 53.38, 119.64, 120.80, 133.47, 133.68, 145.07 and 159.02. Compounds 5b\u20135d have analogous spectra."},{"key":"10.1016\/S0040-4039(00)00755-3_BIB8","unstructured":"Antonini, I.; Franchetti, P.; Grifantini, M.; Martelli, S. J. Heterocycl. Chem. 1976, 13, 111\u2013112; Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1989, 957\u2013960; McNab, H. J. Chem. Soc., Perkin Trans. 1 1987, 653\u2013656; McNab, H.; Thornley, C. J. Chem. Soc., Perkin Trans. 1 1997, 2203\u20132209."},{"key":"10.1016\/S0040-4039(00)00755-3_BIB9","unstructured":"Compound 6 was obtained from the aziridine 3j and TFA (1.2 equiv.) in acetonitrile after heating under reflux for 3 h. Compound 6: mp 150\u2013151\u00b0C (from ether); \u03b4 (300 MHz, CDCl3) 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)."},{"key":"10.1016\/S0040-4039(00)00755-3_BIB10","doi-asserted-by":"crossref","unstructured":"Alves, M. J.; Gilchrist, T. L. Tetrahedron Lett. 1998, 39, 7579\u20137582.","DOI":"10.1016\/S0040-4039(98)01617-7"},{"key":"10.1016\/S0040-4039(00)00755-3_BIB11","unstructured":"The aziridine 8 was isolated as a pale yellow oil (7.5%) by dry flash chromatography; \u03b4 (300 MHz, CDCl3) 1.38 (9H, s), 2.26 (1H, br t, J=10.5 Hz (approx.), NH), 2.41 (1H, d, J3,3\u2032 0, J3,NH=9.9 Hz, 3-H), 2.70 (1H, d, J3\u2032,NH=11.1 Hz, 3\u2032-H), 7.92 (1H, s) and 8.26 (1H, s)."}],"container-title":["Tetrahedron Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403900007553?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0040403900007553?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2019,4,26]],"date-time":"2019-04-26T09:53:57Z","timestamp":1556272437000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0040403900007553"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2000,6]]},"references-count":11,"journal-issue":{"issue":"25","published-print":{"date-parts":[[2000,6]]}},"alternative-id":["S0040403900007553"],"URL":"https:\/\/doi.org\/10.1016\/s0040-4039(00)00755-3","relation":{},"ISSN":["0040-4039"],"issn-type":[{"value":"0040-4039","type":"print"}],"subject":[],"published":{"date-parts":[[2000,6]]}}}