New classes of a,b-unsaturated caprolactams containing variable heteroatoms in d-position were synthesized from heterocyclic imines as a starting material. The synthetic route is based on an acid chloride addition followed by a ring-closing metathesis using a ruthenium catalyst.
First Synthesis of Bi-and Tricyclic α,β-Unsaturated δ-Oxacaprolactams from Cyclic Imines via Ring-Closing Metathesis. -The procedure is based on an acyl chloride addition in the first step, followed by ring-closing metathesis. The lactams are potentially bioactive due to their similarity to known and examined lactams. -(WATZKE, M.; SCHULZ, K.; JOHANNES, K.; ULLRICH, P.; MARTENS*, J.; Eur.
Synthesis of α,β-Unsaturated Caprolactams Starting from Heterocyclic Imines. -Addition of unsaturated acid chlorides (II) to heterocyclic imines (I) followed by reaction with unsaturated nucleophiles (III), (VI), (IX) and subsequent ring closing metathesis afford the α,β-unsaturated caprolactams (V), (VIII) and (XI), containing, sulfur, nitrogen, or selenium atoms in the δ-position. -(JOHANNES, K.; WATZKE, M.; MARTENS*, J.; J.
Fused pyridine derivatives R 0450Synthesis of Bi-and Tricyclic α,β-Unsaturated Lactams as Potential Michael Acceptors Starting from Heterocyclic Imines. -Heterocyclic imines such as (I) are used as starting materials in the three-step synthesis of α,β-unsaturated valerolactams (VII) and (XI). The sequence involves an addition of acid chlorides followed by a modified Hosomi-Sakurai reaction and a final Ru-catalyzed ring closing metathesis. Lactam (VIIa) shows its potential as Michael acceptor in the reaction with thioacetic acid. -(SCHULZ, K.; WATZKE, M.; JOHANNES, K.; ULLRICH, P.; MARTENS*, J.; Synthesis 2009, 4, 665-673; Inst. Pure Appl. Chem., Carl v.
New a,b-unsaturated valerolactams showing potential as Michael acceptors were synthesized from heterocyclic imines as starting materials. The synthetic procedure is based on an acid chloride addition in the first step, followed by a modified HosomiSakurai reaction, and a final ring-closing metathesis using a ruthenium catalyst.
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