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Volumn , Issue 5, 2006, Pages 1251-1255

A new three-component cascade reaction to yield 3-spirocyclopropanated β-lactams

Author keywords

Lactams; Cascade reactions; Cycloadditions; Cyclopropanes; Microwaves; Small rings

Indexed keywords


EID: 33644772154     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500838     Document Type: Article
Times cited : (37)

References (35)
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    • (Ed.: M. I. Page), Blackie Academic & Professional, London
    • d) The Chemistry of β-Lactams (Ed.: M. I. Page), Blackie Academic & Professional, London, 1992.
    • (1992) The Chemistry of β-Lactams
  • 13
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    • The preparation and chemical transformations of methylenecyclopropane (1) and its close relative bicyclopropylidene (2) have been reviewed extensively; a) P. Binger, H. M. Büch, Top. Curr. Chem. 1987, 135, 77-151;
    • (1987) Top. Curr. Chem. , vol.135 , pp. 77-151
    • Binger, P.1    Büch, H.M.2
  • 14
    • 0000494164 scopus 로고    scopus 로고
    • Houben-Weyl, (Ed.: A. de Meijere), Thieme, Stuttgart
    • b) P. Binger, T. Schmidt, in: Methods of Organic Chemistry, (Houben-Weyl), vol. E 17c (Ed.: A. de Meijere), Thieme, Stuttgart, 1997, pp. 2217-2294;
    • (1997) Methods of Organic Chemistry , vol.E 17C , pp. 2217-2294
    • Binger, P.1    Schmidt, T.2
  • 24
    • 11144325118 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2004, 43, 6250-6284, and references therein.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 6250-6284
  • 25
    • 15044345943 scopus 로고    scopus 로고
    • In situ generation of nitrones, especially the unstable one from formaldehyde, for 1,3-dipolar cycloadditions to alkenes, has been used before, see: I. S. Young, J. L. Williams, M. A. Kerr, Org. Lett. 2005, 7, 953-955.
    • (2005) Org. Lett. , vol.7 , pp. 953-955
    • Young, I.S.1    Williams, J.L.2    Kerr, M.A.3
  • 26
    • 33644756857 scopus 로고    scopus 로고
    • note
    • The reactions under microwave heating were carried out in a Smith Creator, part of Coherent Synthesis™ from Personal Chemistry. The used system operated with an emission frequency of 2.45 GHz and a reactor with on-line temperature, pressure and microwave power control. In this apparatus, reactions can be performed at any temperature in the range of 60 to 250°C at pressures of up to 2 MPa (20 bar). The temperature increase can be varied in the range 2-5°C/s, depending on the solvent. The reactions are performed under magnetic stirring, in vials with caps supplied by Personal Chemistry. The instrument processes reaction volumes between 0.5 and 5 mL.
  • 27
    • 33644766104 scopus 로고    scopus 로고
    • note
    • Initially, the reactions were monitored by NMR spectroscopy on aliquots of the crude reaction mixtures, taken from the vials with a syringe.
  • 28
    • 4544307133 scopus 로고    scopus 로고
    • Although not applicable to the synthesis of spirocyclopropanated azetidiones as reported here, another one-pot approach to β-lactams applying nitrones has recently been reported, see: R. Shintani, G. C. Fu, Angew. Chem. 2003, 115, 4216-4219;
    • (2003) Angew. Chem. , vol.115 , pp. 4216-4219
    • Shintani, R.1    Fu, G.C.2
  • 29
    • 0141788715 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 4082-4085.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 4082-4085
  • 30
    • 0001200413 scopus 로고    scopus 로고
    • One of the referees of this article criticized our calling this a "three-component reaction", but we really cannot see the difference between our reaction and the well-known Ugi multi-component reactions in which, according to Ugi's own statement "the starting materials do not react simultaneously in one step, but rather in a sequence of elementary steps, according to a program." See: A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344;
    • (2000) Angew. Chem. , vol.112 , pp. 3300-3344
    • Dömling, A.1    Ugi, I.2
  • 31
    • 0001134412 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3168-3210


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.