A phosphine mediated sequential annulation process of 2-tosylaminochalcones with MBH carbonates to construct functionalized aza-benzobicyclo[4.3.0] derivatives

Abstract

A novel phosphine mediated sequential annulation process to construct functionalized aza-benzobicyclo[4.3.0] derivatives has been developed involving a one-pot sequential catalytic and stoichiometric process, which generates a series of benzobicyclo[4.3.0] compounds containing one quaternary center with up to 94% yield and 20 : 1 dr value. In this reaction, MBH carbonates act as 1,2,3-C synthons.

Silver‐Catalyzed Radical Cascade Cyclization of Unactivated Alkenes towards Cyclopenta[c]quinolines

“…Nitrogen‐containing heterocycles have attracted considerable interest from both medicinal and chemical community, owing to their significant physical, chemical and biological properties . Among them, cyclopenta[ c ]quinoline scaffold (Figure , A ), is the structural core that widely found in various biologically active molecules as well as pharmaceutically promising agents . Examples of such bioactive compounds, as shown in Figure B–F, exhibit a wide variety of pharmacological properties such as antitumor, anti‐inflammatory, antiobesity, and so on .…”

“…[1] Among them, cyclopenta[c]quinoline scaffold (Figure 1, A), is the structural core that widely found in various biologically active molecules as well as pharmaceutically promis-ing agents. [2] Examples of such bioactive compounds, as shown in Figure 1B-F, exhibit a wide variety of pharmacological properties such as antitumor, antiinflammatory, antiobesity, and so on. [3] Due to a longstanding demand on biologically important molecules, development of novel and convenient synthetic methodology to obtain structurally diverse cyclopenta [c] quinolines is urgently pursued and expected in the field of organic synthesis.…”

Lewis-Base-Catalyzed [1 + 2 + 2] Annulation Reaction of Morita–Baylis–Hillman Carbonates with Unsaturated Pyrazolones: Construction of All-Stereogenic Carbon Cyclopentane-Fused Dispiropyrazolones

“…Moreover, after the pioneering work of Lu’s [3 + 2] cycloaddition, MBH carbonates have been used to participate in the reactions as C3 synthons, and various annulation reactions such as [3 + 2], [3 + 3], [3 + 4], and [3 + 6] patterns have been developed. Recently, Huang’s group successfully achieved sequential annulation domino reactions using MBH carbonates as 1,2,3-C3 synthons to construct functionalized multicyclic skeletons . Based on the above prominent work, we believe that divergent reaction pathways may occur with MBH carbonates, depending on the structure and nature of the other reaction partners besides catalysts.…”

Advances in Organophosphorus Redox Catalysis

“…2014 年, Werner 课题组 [20][21] 报道了首例通过 P(III)/ P(V) 氧化还原循环过程实现不对称催化 [26][27] 发展了炔酸酯 与醛基吡咯的加成串联分子内 Wittig 反应来构筑氮杂并 环(Scheme 8B); Kwon 课题组 [28] 发展了联烯酸酯与邻氨 基苯甲醛的 γ-加成串联分子内 Wittig 反应来构筑二氢喹 啉(Scheme 8C); 黄有课题组 [29] 发展了 Morita-Baylis-Hillman (MBH)碳酸酯与邻氨基查耳酮的烯丙基烷基化 串联分子内 Wittig 反应来构筑 6-6-5 并环(Scheme 8D).…”