Synthesis of 1,2-dihydrobenz[c]azepin-3-one via acid-catalyzed cyclization of N-arylmethyl-N-methyl-3-phenylsulfanylacrylamide
Treatment of N-arylmethyl-N-methyl-cis-3-phenylsulfanyl acrylamide (5) with p-toluenesulfonic acid induced two reactions; cyclization to 1,2-dihydrobenz[c]azepin-3-ones (7) and N-dearylmethylation to N-methylacrylamides (9 and 10) depending on the structu
The first successful syntheses of β-lactams via a Pummerer rearrangement of the corresponding sulfoxides are described. Thus, variously substituted 3-(phenylsulfinyl)propionamides were converted to 4-(phenylthio)-2-azetidinones in 14-50% yields with trime
Kaneko
p. 5490 - 5492
(2007/10/02)
Formation of β-lactams from 3-phenylthiopropionamide derivatives. A possible model for penicillin biosynthesis
The Cu-catalysed reaction of the substituted 3-phenylthiopropianamide with di-t-butyl peroxide gives the β-lactam via oxidative cyclisation of the α-thioalkyl radical. Similar reactions of the propionamides with t-butyl perbenzoate give benzoates which can be readily converted into the β-lactams, but neither β-lactams nor benzoates can be obtained from the thiazepines. Dimethyl disulfide is benzoyloxylated on treatment with t-butyl perbenzoate. The relevance of these results to penicillin biosynthesis is discussed.
Beckwith,Easton
p. 3995 - 4001
(2007/10/02)
More Articles about upstream products of 89024-25-9