Simple and condensed β-lactams. Part 29. Synthesis and base-catalyzed ring transformation of 4-[(2RS,3SR)-3-hydroxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl)]thiazol-2(3H)-one

Add time:07/28/2019    Source:sciencedirect.com

4-[(2RS,3RS)-3-Hydroxy- (1b) and -3-(4-chlorophenoxy)-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl]thiazol-2(3H)-one (16b) were synthesised. While the former was smoothly rearranged into (5RS)-5-hydroxy-7-(4-methoxyphenyl)-1,5-dihydrothiazolo[3,4-a]pyrazine-3,6(7H)-dione (7b) on treatment with Na2CO3 under mild conditions, the latter was found to be stable to Na2CO3 under the same conditions. The structural prerequisites for type 1 → 7 ring transformations, including cleavage of the 3–4 bond (azetidin-2-one numbering) of the β-lactam ring are defined.

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