Table 4. Results for the Synthesis of α-Methylidene-γ-lactam-Fused 2,6-Diketopiperazines 8 by a One-Pot Two-Step Sequence.
entry | 1 (R1) | 8 (%)a | drb |
---|---|---|---|
1 | 1a (H) | 8a (33)c (85)d | – |
2 | 1b (Ph) | 8b (77) | >95:5 |
3 | 1c (CH(CH3)2) | 8c (38)c (83)d | >95:5 |
4 | 1d (CH3) | 8d (61) | >95:5 |
5 | 1e (CH2Ph) | 8e (71) | >95:5 |
Chemical yield after purification.
Determined by 1H NMR spectroscopy in the reaction mixture.
Starting from 2-(bromomethyl)acrylic acid.
Starting from 3-bromo-2-(bromomethyl)propionic acid.