Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3 '-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate

Xie Ya-Jing; Sun Jing; Yan Chao-Guo

首页> 外文期刊>RSC Advances >Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3 '-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate

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Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3 '-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate

机译：3-苯并丙二酰亚胺新吲哚与丙二腈或氰基乙酸乙酯反应生成2-氧杂螺[双环[2.2.1]庚烷-6,3'-二氢吲哚]衍生物

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The reaction of malononitrile or ethyl cyanoacetate with two molecules of 3-phencylideneoxindoles in ethanol in the presence of piperidine at room temperature afforded novel 7-(1-benzyl-2-oxoindolin-3-yl)- 2'-oxo-2-oxaspiro[bicyclo[2.2.1]heptane-6,3'-indoline] derivatives in good yields. Under similar reaction conditions, the reaction of cyanoacetamide with 3-phencylideneoxindoles resulted in polysubstituted 4-(2-oxoindolin-3-yl)-2-oxopyrrolidines. The stereochemistry of the reaction was well established by data from H-1 NMR spectra and single crystal structures and a plausible reaction mechanism is rationally proposed.

机译：在哌啶存在下，丙二腈或氰基乙酸乙酯与两个分子的3-苯二甲撑吲哚在乙醇中在室温下反应，得到了新型的7-（1-苄基-2-氧代吲哚-3-基）-2'-氧代-2-氧杂螺[双环[2.2.1]庚烷-6,3'-二氢吲哚]衍生物产率高。在类似的反应条件下，氰基乙酰胺与3-苯并二恶英吲哚的反应产生多取代的4-（2-氧代吲哚-3-基）-氧代吡咯烷。通过H-1 NMR光谱和单晶结构的数据可以很好地确定反应的立体化学，并合理地提出了合理的反应机理。

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《RSC Advances》 |2014年第84期|共10页
作者
Xie Ya-Jing; Sun Jing; Yan Chao-Guo;
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1. Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3 '-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate [J] . Xie Ya-Jing, Sun Jing, Yan Chao-Guo RSC Advances . 2014,第84期

机译：3-苯并丙二酰亚胺新吲哚与丙二腈或氰基乙酸乙酯反应生成2-氧杂螺[双环[2.2.1]庚烷-6,3'-二氢吲哚]衍生物
2. STEREOSELECTIVE EFFICIENT SYNTHESIS OF BICYCLO[2.2.1]HEPTANE DERIVATIVES VIA INTRAMOLECULAR MICHAEL REACTIONS OF VINYL SULFONES [J] . Collins MA., Jones DN. Tetrahedron . 1996,第26期

机译：通过乙烯基砜的分子间迈克尔反应立体合成高效双环[2.2.1]庚烷衍生物
3. Synthesis of spiro[2,3-dihydrofuran-3,3 '-oxindole] derivatives via a multi-component cascade reaction of alpha-diazo esters, water, isatins and malononitrile/ethyl cyanoacetate [J] . Shi Taoda, Teng Shenghan, Wei Yajie, Green chemistry . 2019,第18期

机译：通过α-二氮杂酯，水，甲苷和丙二腈/乙酸乙酯的多组分级联反应来合成螺螺氧[2,3-二氢呋喃-3,3'-氧化吲哚]衍生物
4. Multi Component Reactions under Increased Pressure: On the Mechanism of Formation of Pyridazino543-de16naphthyridine Derivatives by the Reaction of Malononitrile Aldehydes and 2-Oxoglyoxalarylhydrazones in Q-Tubes [O] . Majdah A. AL-Johani, Khadijah M. Al-Zaydi, Sameera M. Mousally, 2017

机译：升高压力下的多组分反应：Q-管中丙二腈醛和2-氧代乙二醛芳基hydr的反应形成吡嗪并543-de 16萘啶衍生物的机理
5. Electrosynthesis of nano-sized pyran and chromene derivatives by one-pot reaction between cyclic-1,3-diketons, malononitrile/ethyl cyanoacetate, and isatins [O] . Mohaddeseh Taheri, Behrooz Mirza, Mohsen Zeeb 2018

机译：纳米吡喃和铬衍生物的一罐反应通过环状-1,3-二酮，丙二腈/乙基氰基乙酸乙酯和甲磺酸盐的一次性反应电气
6. Importance of the Structure of the Phosphorus Functionality in Allowing Dihedral Angle Control of Vicinal 13C-31P Coupling. Carbon-13 NMR Spectra of 7-Substituted Bicyclo(2.2.1)Heptane Derivatives. [R] . Quin, L. D., Littlefield, L. B. 1978

机译：作者：张莹莹，王玮，王莹，工业用水与废水INDUsTRIaL WaTER＆WasTEWaTER侧位13C-31p耦合二面角控制中磷功能结构的重要性。 7-取代双环（2.2.1）庚烷衍生物的碳-13NmR谱。

Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3 '-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate

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