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Synthesis of Derivatives of (1 R *,10a R *)‐1‐Azido‐10‐benzylidene‐4‐(diethylphosphono)‐1,2,10,10a‐tetrahydro‐2‐oxo‐4 H ‐azeto[1,2‐ a ]pyrido[1,2‐ d ]pyrazin‐9‐ylium Bromide
Author(s) -
Hakimelahi Gholam H.,
Sardarian Ali R.
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730121
Subject(s) - chemistry , halogenation , lactam , tricyclic , dimethyl methylphosphonate , medicinal chemistry , stereochemistry , organic chemistry
The synthesis of some derivatives of the title compound VI is described. Bromination of diethyl ( cis ‐3‐azido‐2‐oxo‐4‐styrylazetidin‐1‐yl)(pyridin‐2‐yl)methylphosphonate ( 6 ) in MeOH gave tricyclic β‐lactam 7 , while similar bromination of diethyl ( cis ‐3‐azido‐2‐oxo‐4‐vinylazetidin‐1‐yl)(pyridin‐2‐yl)methylphosphonate ( 9 ) afforded tri‐cyclic β‐lactam 10 . Mechanisms for these transformations are proposed ( Schemes 1 and 2 ).