An Approach to the Synthesis of Spiro[indene-pyridoisoquinoline] Derivatives via 1,4-Dipolar Cycloaddition of Isoquinoline and Acetylene Esters, and (1,3-Dihydro-1,3-dioxo-2H-inden-2-ylidene)malononitrile

Alizadeh Abdolali; Sadeghi Vahideh; Bayat Fahimeh; Zhu Long-Guan

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An Approach to the Synthesis of Spiro[indene-pyridoisoquinoline] Derivatives via 1,4-Dipolar Cycloaddition of Isoquinoline and Acetylene Esters, and (1,3-Dihydro-1,3-dioxo-2H-inden-2-ylidene)malononitrile

机译：通过异喹啉和乙炔酯的1,4-偶极环加成反应和（1,3-二氢-1,3-二氧代-2H-茚满-2-亚烷基）丙二腈合成螺[茚-吡啶基异喹啉]衍生物的方法

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A concise and efficient approach to the spiro-tetrahydroisoquinoline derivatives has been developed by 1,4-dipolar cycloaddition of zwitterions resulting from isoquinoline and acetylene esters and (1,3-dihydro-1,3-dioxo-2H-inden-2-ylidene)malononitrile in MeCN at room temperature. The significance of this method lies in good yields and ease of product purification, and no inert atmosphere is required. The structures of the products were confirmed spectroscopically (IR, H-1- and C-13-NMR, and EI-MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme).

机译：通过由异喹啉和乙炔酯和（1,3-二氢-1,3-二氧代-2H-茚满-2-亚烷基）产生的两性离子的1,4-偶极环加成反应，已开发出一种高效高效的螺-四氢异喹啉衍生物的方法。室温下在MeCN中的丙二腈）该方法的重要性在于高收率和易于产品纯化，并且不需要惰性气氛。产物的结构在光谱学上（IR，H-1-和C-13-NMR，以及EI-MS）和通过元素分析确认。提出了该反应的合理机制（方案）。

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《Helvetica chimica acta》 |2014年第10期|共5页
作者
Alizadeh Abdolali; Sadeghi Vahideh; Bayat Fahimeh; Zhu Long-Guan;
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正文语种 eng
中图分类化学;
关键词
Isoquinoline; Acetylene esters; Propanedinitrile; 2-(1; 3-dihydro-1; 3-dioxo-2H-inden-2-ylidene)-; Spiro-tetrahydroisoquinoline; Cycloadditions;

机译：异喹啉;乙炔酯;丙烷;2-（1;3-二氢-1;3-二氧代-2H-茚满-2-亚烷基）-;螺-四氢异喹啉;环加成;

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1. An Approach to the Synthesis of Spiro[indene-pyridoisoquinoline] Derivatives via 1,4-Dipolar Cycloaddition of Isoquinoline and Acetylene Esters, and (1,3-Dihydro-1,3-dioxo-2H-inden-2-ylidene)malononitrile [J] . Alizadeh Abdolali, Sadeghi Vahideh, Bayat Fahimeh, Helvetica chimica acta . 2014,第10期

机译：通过异喹啉和乙炔酯的1,4-偶极环加成反应和（1,3-二氢-1,3-二氧代-2H-茚满-2-亚烷基）丙二腈合成螺[茚-吡啶基异喹啉]衍生物的方法
2. Facile synthesis of spiro[indoline-3,3'-pyrrolo[1,2-a]quinolines] and spiro- [indoline-3,1'-pyrrolo[2,1-a]isoquinolines] via 1,3-dipolar cycloaddition reactions of heteroaromatic ammonium salts with 3-phenacylideneoxindoles [J] . Lei Wu, Jing Sun, Chao-Guo Yan Organic & biomolecular chemistry . 2012,第47期

机译：通过1,3-偶极环加成轻松合成螺[吲哚啉-3,3'-吡咯并[1,2-a]喹啉]和螺-[吲哚啉-3,1'-吡咯并[2,1-a]异喹啉]芳族铵盐与3-苯并亚甲基吲哚的反应
3. Facile, one-pot synthesis of new phenanthridine derivatives through 1,4-dipolar cycloaddition of phenantridine, activated acetylenes, and aromatic aldehydes [J] . Hossein Mehrabi, Mahdi Hatami-Pour 中国化学快报（英文版） . 2014,第011期

机译：通过菲啶烷，活化的乙炔和芳香醛的1,4-偶极环加成反应，轻松地一锅合成新菲啶衍生物
4. Synthesis of pyrrazoles derivatives via 1,3-dipolar cycloaddition involving sydnone under heating or micro-wawes conditions. [C] . Julie Rivollier, Alain Wagner, Valerie Berl European Symposium on Organic Chemistry . 2009

机译：通过1,3-偶极环加装备来合成吡咯唑衍生物，涉及在加热或微长滑动条件下的Sydnone。
5. Ultrasonic Synthesis Molecular Structure and Mechanistic Study of 13-Dipolar Cycloaddition Reaction of 1-Alkynylpyridinium-3-olate and Acetylene Derivatives [O] . Asmaa Aboelnaga, Mohamed Hagar, Saied M. Soliman 2016

机译：1-羟基炔基-3-吡啶鎓与乙炔衍生物的13-偶极环加成反应的超声合成分子结构及机理研究
6. 1,4-Dipolar cycloaddition in organic synthesis: A facile route to isoquinoline fused heterocycles [O] . Vijay Nair, Anakkalil Ramachandran Sreekanth, Narayana Pillai Abhilash, 2005

机译：有机合成中的1,4-偶极环加成：异喹啉稠合杂环的简便途径
7. Phase Transfer Pd(O) Catalyzed Polymerization Reactions. 1. Synthesis of 1,2-(4,4'-Dialkoxyaryl)Acetylene Monomers and 1,4-Bis(2-(4',4''-Dialkoxyphenyl)Ethynyl)Benzene Derivatives by Phase Transfer Pd(O)/Cu(I) Catalyzed Coupling Reactions. [R] . Pugh, C., Percec, V. 1990

机译：相转移pd（O）催化的聚合反应。 1.相转移pd（O）/ Cu合成1,2-（4,4'-二烷氧基芳基）乙炔单体和1,4-双（2-（4'，4'-二烷氧基苯基）乙炔基）苯衍生物（I）催化的偶联反应。

An Approach to the Synthesis of Spiro[indene-pyridoisoquinoline] Derivatives via 1,4-Dipolar Cycloaddition of Isoquinoline and Acetylene Esters, and (1,3-Dihydro-1,3-dioxo-2H-inden-2-ylidene)malononitrile

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