- A direct link between the Passerini reaction and α-lactams
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α-Lactams (aziridinones) can function to replace two of the three reactants, the oxo-compound and the isonitrile, in the Passerini reaction. Four α-lactams (5a-d) were reacted with mono- and dicarboxylic acids of positive pKa values to give 2-acyloxycarboxamides (4) and bis-2-acyloxycarboxamide products 12 and 13, respectively. The same compounds were also prepared via the Passerini reaction. Acids with a negative pK a decarbonylate α-lactams to give immonium salts. The main path of the reaction depends on the pKa of the acid component, the reactivity of the α-lactam, and the reaction conditions.
- Lengyel, István,Cesare, Victor,Taldone, Tony
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- The synthesis, physical, and spectral properties, and some reactions of a new stable bis-α-lactam (aziridinone) with a terpene skeleton
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A synthesis of a new stable bis-α-lactam, cis-1,1′(p-menth-1,8-ylene) bis(3-tert-butyl-2-azirididone) (4), derived from p-menthane, is described. Complete spontaneous thermal decomposition required lh of reflux in boiling n-decane (b.p. 174°C) and the products are 2,2-dimethylpropanal (pivalaldehyde) (6) and 1,8-diisocyano-p-menthane (7). Reaction with benzylamine yielded the unexpected bis-benzylamide (13a), while reaction with sodium methoxide gave the bisα-amino acid ester (14).
- Lengyel,Cesare,Taldone,Uliss
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p. 3671 - 3683
(2007/10/03)
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