Reactions of 3,4-dihydroisoquinolines and dihydrothieno[3,2-c]pyridines with benzyne

Guranova, Natalia; Varlamov, A. V.; Ilyushenkova, Valentina V.; Соколова, Е. А.; Борисова, Т. Н.; Аксенов, А. В.; Khrustalev, Victor N.; Voskressensky, Leonid G.

doi:10.1016/j.mencom.2017.09.026

Cited by 5 publications

(3 citation statements)

References 30 publications

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“…In 2017, Tian and co-workers demonstrated a three-component carboarylation reaction of arynes, imines, and various carbon nucleophiles, such as chloroform, acetonitrile, and methyl propiolate, and obtained products 8-61 (Scheme a) . Meanwhile, Voskressensky et al synthesized cyanomethyl-substituted tetrahydroisoquinolines and tetrahydrothieno[3,2- c ]pyridines 8-63 through the MCR of the dihydro analogues of isoquinoline and pyridine 8-62 with benzyne and acetonitrile (Scheme b) . A four-component reaction was also developed through the in situ generation of imines from primary amines and aldehydes .…”

Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

“…In 2017, Tian and coworkers demonstrated a three-component carboarylation reaction of arynes, imines, and various carbon nucleophiles, such as chloroform, acetonitrile, and methyl propiolate, and obtained products 8-61 (Scheme 132a). 584 585 A four-component reaction was also developed through the in situ generation of imines from primary amines and aldehydes. 586 In a study carried out by Tian, Yu, and co-workers on the MCRs of arynes with electron-deficient N-heteroaromatics, they also realized similar transformations with imines using carbon tetrachloride as the third component, giving rise to products 8-64 (Scheme 132c).…”

Section: Isocyanide-triggered Mcrsmentioning

confidence: 99%

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o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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Arynes are among the most active organic intermediates and have found numerous applications in expeditious preparation of substituted arenes. In the past 20 years, chemists have witnessed a resurgence in aryne chemistry, which is mainly attributed by the extensive utilization of Kobayashi's method, a fluoride-induced removal of the TMS group with concomitant departure of its ortho OTf group on o-silylaryl triflates. Nowadays, o-silylaryl triflates are the most frequently employed aryne precursors. This review provides an overview of the history of Kobayashi's method, its methodological achievements, and its applications in the synthesis of natural products, bioactive molecules, and polycyclic aromatic hydrocarbons.

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Section: Multicomponent Reactions (Mcrs)mentioning

confidence: 99%

Section: Isocyanide-triggered Mcrsmentioning

confidence: 99%

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

2021

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“…2017 年, 田仕凯课题组 [79] 报道了芳炔、亚胺和各种碳亲核试剂(如氯仿、乙腈和丙酸甲酯)的三组分反应 (Scheme 61). 同年, Voskressensky 课题组 [80] 报道了芳炔、乙腈和异喹啉或吡啶的二氢类似物的三组分反应 (Scheme 62), 高产率地合成了氰甲基取代的四氢异喹啉和四氢噻吩吡啶.…”

Section: 芳炔参与的氮芳基化三组分反应unclassified

Recent Progress on Arylation with Aryne through Three-Component Reaction

Chen¹,

Yang²,

Li³

et al. 2023

Chinese Journal of Organic Chemistry

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The three component reaction has the advantages of simple operation and efficient reaction, in line with the principles of atomic economy and green environmental protection. At present, the arylation without transition metal catalyst is mainly divided into three types of as following: (1) the direct arylation, (2) the insertion of aryne into σ-bond or π-bond, and (3) the three-component reactions involving aryne. Compared with the direct arylation and the insertion of aryne into σ-bond or π-bond, the mechanism of three component reactions involving aryne is still unclear, and the published reviews are still lacking. In order to facilitate the scientific researchers to consult and understand the three-component reaction involved in aryne, the progresses in the three-component reaction involving aryne in recent years are reviewed. Keywords aryne; three component reaction; carbon and heteroatom; arylation 芳炔作为一类重要的反应活性中间体一直备受人们的关注, 其参与的反应为构建碳-碳键和碳-杂键提供了新的反应模式 [1][2][3][4][5][6] , 并且在天然产物、生物碱和药物中间体的合成中具有广泛的应用 [7] . 自 1983 年 Kobayashi 课题组 [8] 首次报道 2-(三甲基甲硅烷基)苯基三氟甲磺酸酯为苯炔前体, 在氟负离子作用下高效生成苯炔的方法以来(Scheme 1), 芳炔参与的芳基化反应推动了芳炔化学的快速发展.

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Sustainable Domino C−N/C−C Bond Formation with Outstanding E Factors and High Volume Productivity

Hwu,

Gupta,

Panja

et al. 2024

Eur J Org Chem

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One of the primary concerns in the development of new chemical reactions pertains to the choice of solvents, many of which can have harmful ecological impacts. Additionally, a major portion of waste generated in the chemical and pharmaceutical industries comes from the solvents employed. The elimination of solvent usage is highly desirable for creation of environmentally friendly chemical processes as it leads to a substantial reduction in waste production. Accordingly, a novel neat reaction was developed for the synthesis of (β‐amino)nitriles as a prominent moiety through a domino process. It involved the use of silylphenyl triflates, Schiff bases, and acetonitrile (CH₃CN) in a 1:1:1 ratio, with CH₃CN served as a starting material rather than a solvent. This reaction was initiated by caesium fluoride (CsF) to form an aryne through 1,2‐elimination followed by sequential 1,2‐addition, proton transfer, and a second 1,2‐addition. Complete conversion was carried out at 25 °C for 1.0 h to give (β‐amino)nitriles in 76–88% yields. This solvent‐free reaction minimized waste production and reduced costs associated with extra reagents, solvents, and labour. It possesses a compelling E factor and impressive volume productivity. This reaction sets a new benchmark for solvent‐free aryne domino processes in green chemistry advancements.

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Reactions of 3,4-dihydroisoquinolines and dihydrothieno[3,2-c]pyridines with benzyne

Cited by 5 publications

References 30 publications

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

o-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors

Recent Progress on Arylation with Aryne through Three-Component Reaction

Sustainable Domino C−N/C−C Bond Formation with Outstanding E Factors and High Volume Productivity

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