First one-pot stereoselective synthesis of cis-2,3-dihydro-4-perfluoroalkyl-1H-1,5-benzodiazepines via a catalyst-free three-component reaction

Xu, Jiechao; Wei, Jiao; Bian, Linglin; Zhang, Jiaping; Chen, Jie; Deng, Hongmei; Wu, Xiaoyu; Zhang, Hui; Cao, Weiguo

doi:10.1039/c0cc05039c

Cited by 31 publications

(11 citation statements)

References 38 publications

(2 reference statements)

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“…The electronic effect of substituents efficiently alters the yield of the ectron-withdesired product. Electron-releasing groups on aldehydes provide much better results than electronwithdrawing groups [263].…”

Section: Synthesis Of Diazepinesmentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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One-pot heterocyclic synthesis is an exciting research area as it can open routes for the development of otherwise complex transformations in organic synthesis. Heterocyclic compounds show wide spectrum of applications in medicinal chemistry, chemical biology, and materials science. These heterocycles can be generated very efficiently through highly economical and viable routes using one-pot synthesis. In particular, the metal-free one-pot synthetic protocols are highly fascinating due to several advantages for the industrial production of heterocyclic frameworks. This comprehensive review is devoted to the transition metal-free one-pot synthesis of nitrogen-containing heterocycles from the period 2010-2013.

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Section: Synthesis Of Diazepinesmentioning

confidence: 99%

Transition metal-free one-pot synthesis of nitrogen-containing heterocycles

et al. 2015

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“…Thus, we developed a first stereoselective synthesis of perfluoroalkylated 1,5-benzodiazepines 85 via a one-pot, catalyst-free, three-component reaction, using methyl perfluoroalk-2-ynoates 1 as the key building blocks (Scheme 26). [44] Both aromatic and aliphatic aldehydes 83 reacted readily with o-phenylenediamine 84 and methyl perfluoroalk-2-ynoates 1 to afford the corresponding 85. The experimental results also indicated that this reaction was The high stereoselectivity shown in this cascade reaction could be explained by the pathway in Scheme 27.…”

Section: P E R S O N a L A C C O U N T T H E C H E M I C A L R E C O R Dmentioning

confidence: 99%

Synthesis of Organofluoro Compounds Using Methyl Perfluoroalk-2-ynoates as Building Blocks

Sun

Han

Chen

et al. 2016

The Chemical Record

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This review provides an overview of several synthetic applications of methyl perfluoroalk-2-ynoates, leading to convenient preparation of many perfluoroalkylated compounds. The use of these important substrates in the synthesis of various five-, six-, and seven-membered heterocycles, cyclopentadienes, and biphenyls is described, alongside a discussion of the mechanistic aspects of these reactions.

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“…在以往文献报道 [3,8,9] 和我们自己工作的基础上, 推断反应机理如 Scheme 1. [8] 138.3, 136.8, 134.9, 134.6, 133.4, 133.1, 131.6, 130.6, 130.5, 129.4, 128.5, 123.4, 120.3 (q, 1 J C -F ＝275 Hz), 38. 4,135.7,134.4,129.8,129.1,123.55,119.6 (m,CF 3 [11] …”

Section: 结果与讨论unclassified

“…然而目前有关氟代烷基直接取代在杂环部位的 1,5-苯并二氮-2-酮类化合物的合成的报道却很少, 主要是采用氟砌块策略, 用三氟乙酰乙酸乙酯与邻苯二胺在近 150 ℃条件下缩合得到三氟甲基取代的 1,5-苯并二氮-2-酮 [7] . 2011 年, 本课题组报道了以含氟炔酸甲酯为含氟砌块, 与邻苯二胺和芳醛一锅法合成了一系列多氟烷基取代的 1,5-苯并二氮 衍生物 [8] . 这里, 本文在前面工作的基础上, 在没有催化剂存在条件下, 使含氟炔酸甲酯与邻芳基二胺在无水甲苯中 80 ℃反应 24 h, 即得到 4-多氟烷基-1,5-苯并二氮-2-酮类化合物.…”

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