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Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132
Graphical Abstract
Scheme 1: Preparation of α-(o-nitrobenzoyl)-β-enamino amides 3. Reagents and conditions: i) EtNH2 (70% aq, 1....
Scheme 2: Alternative manipulations of intermediates 3, leading to either 2-alkyl-4-quinolones 8 (via enamino...
Beilstein J. Org. Chem. 2018, 14, 2602–2606, doi:10.3762/bjoc.14.238
Scheme 1: Preparation of α-C-acylated β-enamino amides 3 and 4. Reagents and conditions: 2, NMM, EtOCOCl, CH2...
Scheme 2: Domino fragmentation of 3 to β-keto amides 5 with competing cyclisation to pyrrolin-4-ones 6. Reage...
Scheme 3: Proposed mechanism for the formation of side products 6.
Scheme 4: Proposed mechanism for the formation of the target β-keto amides 5.
Scheme 5: Reactivity of analogues 9, lacking the auxiliary amino group [34].
Scheme 6: Domino fragmentation of compounds 4 (R2 = R3 = H) to N-protected ω-amino-β-keto amides 11.
Scheme 7: Ring–chain tautomerism in compounds 11b,c,f,j (n = 2) and reduction to the corresponding β-hydroxy ...