Thietane-fused β-Lactams via Photochemical Cycloaddition Reaction of N-(α,β-Unsaturated Carbonyl)thioamides
Photolysis of N-(α,β-unsaturated carbonyl)thioamides gave thietane-fused β-lactams in good yields, whereas some of the thioimides formed thiones via β-hydrogen abstraction of the thiocarbonyl group.Substituents at the α-position to the carbonyl carbon lead to a preference for cyclization over β-hydrogen abstraction.From a sensitisation experiment this reaction was shown to proceed via an n?* triplet excited state.
A New Synthesis of β-Lactams: 3-Oxo-6-thia-2-azabicyclohexanes via Photochemical Reactions of N-(Thiobenzoyl)methacrylamides
Irradiation of N-(thiobenzoyl)methacrylamides in benzene gave thietan-fused β-lactams in good yields, and these were converted to other β-lactams by reduction or oxidation.
Sakamoto, Masami,Omote, Yoshimori,Aoyama, Hiromu
p. 396 - 397
(2007/10/02)
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