丙二腈参与的多组分串联反应研究
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摘要
多组分反应(MCRs)是一种高效的一步合成法,几种(三种或以上)简单易得的组分通过一步合成得到一个单一的化合物。多组分反应由于其灵活性、会聚性和原子经济性,与线性合成法、分步合成法相比显示出很多优越性,因此在很多领域如有机化学,医药化学和组合化学中得到了广泛的应用。丙二腈是常见的简单化学试剂。丙二腈分子内含有两个氰基官能团,具有强吸电子能力。氰基的碳氮三键非常适合亲核加成反应,同时对于取代反应,氰基又是一个非常好的离去基团。由于两个氰基的吸电子作用,使得丙二腈分子中亚甲基上的两个氢原子相当活跃。因此,丙二腈分子中有多个反应位点,是非常理想的多组分反应底物之一。为此我们开展了以丙二腈为反应物之一的新的多组分反应研究,取得了一些有意义的成果:
1.用丙二腈和芳香醛反应得到的芳亚甲基丙二腈(olefin)和活泼吡啶季铵盐(溴化N-乙酸乙酯基吡啶、溴化N-苯乙酮基吡啶和氯化N-N’, N’-二乙基乙酰胺基吡啶)反应,得到了相应的多取代环丙烷化合物。通过IR、NMR等方法进行了结构表征,并用单晶衍射方法测定其中五个多取代环丙烷的晶体结构。
2.以丙二腈、芳香醛、溴乙酸乙酯(氯乙酸甲酯)和吡啶为底物,在乙腈中用吡啶做碱的多组分反应生成了相应的未见报道的多取代苯化合物。通过IR、NMR、元素分析等方法进行了结构表征,并用单晶衍射方法测定其中五个多取代苯化合物的晶体结构。
3.以丙二腈、芳香醛、氯乙腈和吡啶为底物,在氮气保护下,在乙腈中用吡啶做碱的多组分反应生成了相应的未见报道的多取代苯并含氮杂环化合物以及中间产物2个。通过IR、NMR、元素分析等方法进行了结构表征,并用X-Ray测定其中八个含氮杂环化合物的晶体结构。
Multicomponent reactions (MCRs) are one-pot processes in which several easily accessible components react to form a single product. They offer significant advantages over conventional linear-type syntheses due to their flexible, convergent and atom efficient nature and have become an important area of research in organic, medicinal and combinatorial chemistry. Malononitrile is an exceptionally versatile compound and is therefore used extensively as a reactant or reaction intermediate. It exhibits unique reactivity since the strongly electron-withdrawing cyano groups activate the methylene group, their polar multiple bond is suitable for nucleophilic addition and is also a good leaving group for substitution. This exceptional behavior makes malononitrile an important candidate for the design of new practical multicomponent reaction procedures. So we developed some new one-pot multicomponent reactions with malononitrile as one of the components in the reaction and found some intriguing results.
1. Malononitrile was condensed with aromatic aldehydes to give arylidenemalononitriles in basic conditions, which were reacted with pyridinium saltes (N-ethoxycarbonylmethylpyridium bromide, N-phenacylpyridinium bromide, and N-N’, N’-diethylaminocarbonylmethylpyridinium chloride) to give corresponding polysubstituted cyclopropanes. The polysubstituted cyclopropanes were fully characterized by NMR, IR spectra. The single crystal structures of five cyclopropanes were determined by X-ray diffraction method.
2. Unprocedent polysubstituted benzene derivatives were produced in multi-component cyclization reactions of pyridine, ethylα-bromoacetate (methylα-chloroacetate), malononitrile and aromatic aldehydes in refluxing acetonitrile. The polysubstituted benzene derivatives were fully characterized by NMR, IR spectra and were confirmed by X-ray diffraction determined of five single crystal structures of polysubstituted benzene derivatives.
3. Novel polysubstituted benzene derivatives and nitrogen containg heterocyclic compounds were produced in a multi-component cyclization reaction of pyridine, chloroacetonitrile, malononitrile and aromatic aldehydes in refluxing acetonitrile under the protection of nitrogen. All the compounds were fully characterized by NMR, IR spectra. the single crystal structure of six compounds and two intermediate compounds were determined by X-ray diffraction method.
1.用丙二腈和芳香醛反应得到的芳亚甲基丙二腈(olefin)和活泼吡啶季铵盐(溴化N-乙酸乙酯基吡啶、溴化N-苯乙酮基吡啶和氯化N-N’, N’-二乙基乙酰胺基吡啶)反应,得到了相应的多取代环丙烷化合物。通过IR、NMR等方法进行了结构表征,并用单晶衍射方法测定其中五个多取代环丙烷的晶体结构。
2.以丙二腈、芳香醛、溴乙酸乙酯(氯乙酸甲酯)和吡啶为底物,在乙腈中用吡啶做碱的多组分反应生成了相应的未见报道的多取代苯化合物。通过IR、NMR、元素分析等方法进行了结构表征,并用单晶衍射方法测定其中五个多取代苯化合物的晶体结构。
3.以丙二腈、芳香醛、氯乙腈和吡啶为底物,在氮气保护下,在乙腈中用吡啶做碱的多组分反应生成了相应的未见报道的多取代苯并含氮杂环化合物以及中间产物2个。通过IR、NMR、元素分析等方法进行了结构表征,并用X-Ray测定其中八个含氮杂环化合物的晶体结构。
Multicomponent reactions (MCRs) are one-pot processes in which several easily accessible components react to form a single product. They offer significant advantages over conventional linear-type syntheses due to their flexible, convergent and atom efficient nature and have become an important area of research in organic, medicinal and combinatorial chemistry. Malononitrile is an exceptionally versatile compound and is therefore used extensively as a reactant or reaction intermediate. It exhibits unique reactivity since the strongly electron-withdrawing cyano groups activate the methylene group, their polar multiple bond is suitable for nucleophilic addition and is also a good leaving group for substitution. This exceptional behavior makes malononitrile an important candidate for the design of new practical multicomponent reaction procedures. So we developed some new one-pot multicomponent reactions with malononitrile as one of the components in the reaction and found some intriguing results.
1. Malononitrile was condensed with aromatic aldehydes to give arylidenemalononitriles in basic conditions, which were reacted with pyridinium saltes (N-ethoxycarbonylmethylpyridium bromide, N-phenacylpyridinium bromide, and N-N’, N’-diethylaminocarbonylmethylpyridinium chloride) to give corresponding polysubstituted cyclopropanes. The polysubstituted cyclopropanes were fully characterized by NMR, IR spectra. The single crystal structures of five cyclopropanes were determined by X-ray diffraction method.
2. Unprocedent polysubstituted benzene derivatives were produced in multi-component cyclization reactions of pyridine, ethylα-bromoacetate (methylα-chloroacetate), malononitrile and aromatic aldehydes in refluxing acetonitrile. The polysubstituted benzene derivatives were fully characterized by NMR, IR spectra and were confirmed by X-ray diffraction determined of five single crystal structures of polysubstituted benzene derivatives.
3. Novel polysubstituted benzene derivatives and nitrogen containg heterocyclic compounds were produced in a multi-component cyclization reaction of pyridine, chloroacetonitrile, malononitrile and aromatic aldehydes in refluxing acetonitrile under the protection of nitrogen. All the compounds were fully characterized by NMR, IR spectra. the single crystal structure of six compounds and two intermediate compounds were determined by X-ray diffraction method.
引文
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