College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon, 21983, Republic of Korea.
Org Biomol Chem. 2020 Dec 23;18(48):9836-9851. doi: 10.1039/d0ob02002h.
A highly efficient synthetic route to a new 1,4-diazepene skeleton, 2-acyl-4-aryl-5H-pyrrolo[1,2-d][1,4]diazepine, was established where Knoevenagel condensation of readily available two fragments, N-substituted pyrrole-2-carboxaldehyde and α-azidoketone, followed by intramolecular aza-Wittig reaction under Staudinger azide reduction conditions permitted facile access to a poly-substituted 1,4-diazepine ring system for the first time. Successful application of this protocol to construct new 1-alkoxy-3-acylisoquinolines and 1-alkoxy-3-acyl-β-carbolines is also demonstrated.
建立了一种高效的合成新 1,4-二氮杂环庚烷骨架的方法，即 2-酰基-4-芳基-5H-吡咯并[1,2-d][1,4]二氮杂环，其中 Knoevenagel 缩合反应可使易得的两个片段（N-取代的吡咯-2-甲醛和α-叠氮酮）发生反应，然后在 Staudinger 叠氮还原条件下进行分子内氮杂 Wittig 反应，首次可轻松获得多取代的 1,4-二氮杂环庚烷环系。还成功应用该方案构建了新的 1-烷氧基-3-酰基异喹啉和 1-烷氧基-3-酰基-β-咔啉。
