A mild method of introducing 7α-alkoxy in cephalosporins

Abstract

A mild method of introducing 7a-alkoxy in cephalosporins was developed. An electrophilic center was formed at the C-7 position of 7-substituted-azino-cephalosporins with the help of a nitro group via the conjugated system. The lower alkoxy groups (including C1-C3 alkyl and Bu) were stereoselectively introduced into the C-7a position under mild conditions from the corresponding alcs., in the presence of protic acids. tert-Bu alcohol and its higher homologs do not react. Twelve new benzyhydryl esters of 7a-alkoxy-7b-hydrazonocephalosporins I (R = H, OAc, methyltetrazolylthio; R1 = nitrophenyl, nitrothienyl, nitrofuryl; R2 = Me, Et, Pr, Me2CH, Bu) were synthesized, the structures of which were identified with UV, IR, 1H NMR and mass spectra.

Key words: ULTRAVIOLET SPECTROPHOTOMETRY, ALKOXYL GROUP, INFRARED SPECTROPHOTOMETRY, MASS SPECTROGRAPHY, PROTON MAGNETIC RESONANCE SPECTROMETRY, MONOHYDRIC ALCOHOL, CEPHALOSPORINS

CLC Number:

O629

Cite this article

SUN KUAILIN;LI RUNSUN. A mild method of introducing 7α-alkoxy in cephalosporins[J]. Chin. J. Org. Chem., 1989, 9(2): 166-170.

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