Yb(OTf)<sub>3</sub>‐Catalyzed Cycloaddition/[3,3]‐Rearrangement of <i>N</i>‐Vinyl‐α,β‐Unsaturated Ketonitrones with Methylenecycloprop‐anes: Stereoselective Synthesis of Nine‐Membered Nitrogen Heterocycles

Ma, Xiao‐Pan; Nong, Cai‐Mei; Zhao, Jie; Lu, Xiuqiang; Liang, Cui; Mo, Dong‐Liang

doi:10.1002/adsc.201901206

Cited by 17 publications

(4 citation statements)

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“…6). 2017 年, 赵宇教授课题组 [33] 2020 年, Shibata 课题组 [38] 2021 年, 郭武生课题组 [40] 2022 年, 郭红超课题组 [42] 发展了一种新型的 δ-乙 2019 年, 莫冬亮课题组 [46] 利用相似的策略, 通过 2020 年, 莫冬亮课题组 [47] 报道了 Yb(OTf 1 Yb(OTf)3 catalyzed cycloaddition and rearrangement to form nine-membered N-heterocycles a cis/trans ratio, as determined by 1 H NMR analysis of the crude reaction mixture. 2020 年, 莫冬亮课题组 [48] 报道了 Yb(OTf 2021 年, 莫冬亮课题组 [49] 报道了通过银(I)催化的 N-烯基-α,β-不饱和硝酮 72 与手性 3-丙酰噁唑烷-2-酮 80…”

Section: 分子间环加成构建九元氮杂环化合物unclassified

Recent Advances on the Synthesis of Nine-Membered N-Heterocycles

Qin¹,

Zou²,

Nong³

et al. 2023

Chinese Journal of Organic Chemistry

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Nine-membered N-heterocycle scaffolds are widely found in natural products and biologically active molecules. The rigid structure of the medium-sized ring plays important roles in the regulation of their biological and pharmacological activities. Therefore, nine-membered N-heterocycle is one of the most attractive medium-sized ring compounds. Because of the increasing entropy and ring extension of nine-membered ring skeleton, the synthesis of nine-membered N-heterocycles is still difficult; especially the effective control of substituent stereoselectivity for the nine-membered ring is one of the greatest challenging topics This review summarizes the novel synthetic strategies of nine-membered N-heterocycles and their applications in the synthesis of natural products and pharmaceutically active molecules containing nine-membered ring scaffold in recent years. Keywords nine-membered N-heterocycles; medium-sized ring compounds; cyclization; cycloaddition; ring expansion 氮杂环结构广泛存在天然产物和药物分子中, 是新药设计和分子药理活性研究中的优势骨架 [1] . 中环骨架 (8～12 元环)的氮杂环化合物在自然界中广泛存在, 由于环张力和熵增不利的影响, 中环骨架化合物的构建一直是有机合成中极富挑战的难点之一 [2] . 其中, 九元氮杂环化合物是最被关注的中环化合物之一 [3] . 如生物碱 antaroide [4] , (±)-cleavamine [5] , melohenine B [6] , (＋)-lycoposerramine B [7] , (-)-rhazinilam [8] , palhinine A [9] 等(图 1).

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Section: 分子间环加成构建九元氮杂环化合物unclassified

Recent Advances on the Synthesis of Nine-Membered N-Heterocycles

Qin¹,

Zou²,

Nong³

et al. 2023

Chinese Journal of Organic Chemistry

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“…12). 图式 23 N-烯基-α,β-不饱和硝酮构建氮杂九元环化合物 Scheme 23 Construction of nine-membered heterocycles from N-vinyl-α,β-unsaturated nitrones 2020 年, 莫冬亮课题组 [39] 报道了 Yb(OTf) 3 催化下…”

Section: N-烯基-αβ-不饱和硝酮构建氮杂九元环化合物unclassified

Advances on the Synthesis and Application of α,β-Unsaturated Nitrones

Zou¹,

Qin²,

Wang³

et al. 2021

Chinese Journal of Organic Chemistry

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Nitrones, served as one of the most important 1,3-dipoles in organic synthetic chemistry, can participate in various organic synthetic reactions to synthesize various heterocyclic compounds, such as nucleophilic addition, cycloaddition reaction, rearrangement reaction, C-H bond activation, etc. They are very important organic building blocks for the further construction of complex molecules. In recent years, α,β-unsaturated nitrone has attracted widespread attention from synthetic chemists because of its α,β-unsaturated bond containing rich chemical transformations, and can take part in various new chemical conversions to construct new structural heterocyclic compounds. The new strategies for the preparation of α,β-unsaturated nitrones in the past ten years, and their applications to construct nitrogen heterocyclic compounds, including O-transfer reaction, addition of nucleophiles and radical reagents, and various cycloaddition reactions, are reviewed.

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“…Based on the interest in cycloaddition of our group, we surmised that intermolecular cycloaddition of ao-QMs with furans would afford tetrahydrofuro[3,2- b ]quinolines, owing to the richer electron cloud density at the α-position of furans (Scheme D). Then, a complete regioselectivity of cycloaddition of ao-QMs with furans will be achieved compared to intermolecular cycloaddition reported by Corey and co-workers in Scheme B.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Furo[3,2-b]quinolines and Furo[2,3-b:4,5-b′]diquinolines through [4 + 2] Cycloaddition of Aza-o-Quinone Methides and Furans

et al. 2020

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An approach for the construction of furo[3,2-b]quinolines and furo[2,3-b:4,5-b′]diquinolines is developed through a metal-free [4 + 2] cycloaddition of easily available in situ generated aza-o-quinone methides and furans. The reaction tolerates a wide range of aza-o-quinone methides and substituted furans to afford the corresponding dihydro- or tetrahydrofuroquinolines in good to excellent yields. Mechanistic studies reveal that the reaction involves a concerted [4 + 2] cycloaddition pathway and shows a high regioselectivity of cycloaddition for a furan ring. The present method features mild reaction conditions, dearomatization of furans, high regio- and diastereoselectivity, gram-scalable preparations, and diversity of furoquinolines.

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Yb(OTf)₃‐Catalyzed Cycloaddition/[3,3]‐Rearrangement of N‐Vinyl‐α,β‐Unsaturated Ketonitrones with Methylenecycloprop‐anes: Stereoselective Synthesis of Nine‐Membered Nitrogen Heterocycles

Cited by 17 publications

References 60 publications

Recent Advances on the Synthesis of Nine-Membered N-Heterocycles

Recent Advances on the Synthesis of Nine-Membered N-Heterocycles

Advances on the Synthesis and Application of α,β-Unsaturated Nitrones

Synthesis of Furo[3,2-b]quinolines and Furo[2,3-b:4,5-b′]diquinolines through [4 + 2] Cycloaddition of Aza-o-Quinone Methides and Furans

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Yb(OTf)3‐Catalyzed Cycloaddition/[3,3]‐Rearrangement of N‐Vinyl‐α,β‐Unsaturated Ketonitrones with Methylenecycloprop‐anes: Stereoselective Synthesis of Nine‐Membered Nitrogen Heterocycles

Cited by 17 publications

References 60 publications

Recent Advances on the Synthesis of Nine-Membered N-Heterocycles

Recent Advances on the Synthesis of Nine-Membered N-Heterocycles

Advances on the Synthesis and Application of α,β-Unsaturated Nitrones

Synthesis of Furo[3,2-b]quinolines and Furo[2,3-b:4,5-b′]diquinolines through [4 + 2] Cycloaddition of Aza-o-Quinone Methides and Furans

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Yb(OTf)₃‐Catalyzed Cycloaddition/[3,3]‐Rearrangement of N‐Vinyl‐α,β‐Unsaturated Ketonitrones with Methylenecycloprop‐anes: Stereoselective Synthesis of Nine‐Membered Nitrogen Heterocycles