Microwave-assisted rapid synthesis of α-amino-β-lactams

A rapid and convenient approach to α-amino-β-lactams has been developed using the tetrachlorophthalimido group as a masked amino substituent. Reaction between glycine and tetrachlorophthalic anhydride in DMF for about 90 sec in a domestic microwave oven led to an imidoacetic acid in high yield; the...

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Bibliographic Details
Published inTetrahedron letters Vol. 37; no. 39; pp. 6989 - 6992
Main Authors Bose, Ajay K, Jayaraman, M, Okawa, A, Bari, S.S, Robb, E.W, Manhas, M.S
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.09.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A rapid and convenient approach to α-amino-β-lactams has been developed using the tetrachlorophthalimido group as a masked amino substituent. Reaction between glycine and tetrachlorophthalic anhydride in DMF for about 90 sec in a domestic microwave oven led to an imidoacetic acid in high yield; the corresponding acid chloride reacted with Schiff bases to provide mixtures of trans and cis β-lactams. Nearly exclusive formation of trans β-lactams could be achieved in some cases in a few minutes by conducting β-lactam formation under strong microwave irradiation. Facile conversion to α-amino-β-lactams was realized in 5–10 minutes via solventless reaction of these α-amino-β-lactams with ethylenediamine at room temperature. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01571-7