A novel stereoselective method for the introduction of a methoxy (alkoxy) group into the 6 α-position of penicillins

Abstract

6a-Alkoxy-6b-hydrazonopenicilins I (R = PhCH2, Me3CCO2CH2, CH2:CHCH2; R1 = Me, Et, Pr, Me2CH, MeOCH2CH2; X = O, S, vinylene) were prepared by reaction of 6-hydrazonopenicillin with aromatic aldehydes II (X = O, S, vinylene) in R1OH in the presence of protic acid at room temperature to form 6-arom. substituted azinopenicillins. Nucleophilic attack of R1OH on C-6 of the latter compounds, due to activation by the nitro group, gave I.

Key words: PENICILLIN, METHOXY GROUP, METHOXY GROUP, STEREOSELECTIVITY, LACTAM, ADDITION REACTION, CEPHALOSPORINS

CLC Number:

O629
R914

Cite this article

ZHONG YILI;LI RUNSUN;LEI XINGHAN. A novel stereoselective method for the introduction of a methoxy (alkoxy) group into the 6 α-position of penicillins[J]. Chin. J. Org. Chem., 1989, 9(1): 69-72.

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在青霉素上立体选择引入6α-甲(烷)氧基的新方法