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Reactions of 3‐(Prop‐2‐enylidene)azetidin‐2‐ones with 4,5‐Dihydro‐3 H ‐1,2,4‐triazole‐3,5‐diones
Author(s) -
Ruf Sabine,
Otto HansHartwig
Publication year - 1996
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.19960790715
Subject(s) - chemistry , cycloaddition , stereoselectivity , derivative (finance) , adduct , stereochemistry , medicinal chemistry , triazole , organic chemistry , catalysis , financial economics , economics
The 3‐(2‐propenylidene)‐β‐lactams 1a–c react as semicyclic dienes with the dihydrotriazole‐diones 2 in a stereoselective fashion leading to the cycloadducts 3 . The 3′,3′‐disubstituted derivative 4 gives no [4 + 2]‐cycloaddition products but forms the adducts 5 and 6 . Sterochemistry and reaction pathways are discussed.