摘要
杂环化合物是一类具有生物活性、医学价值的重要物质。对其合成方法的研究一直是人们关注的重要课题。最近这些年来,多组分反应(MCRs)由于其过程简单,高效且具有较高的原子经济性而得到广泛的研究。这种由3个或3个以上的起始原料一锅煮反应的合成方法,为快速合成具有结构多样性和复杂性的杂环化合物提供了一个强有力的工具。为此,我们课题组也开展了一系列以多组分反应合成杂环化合物的研究。
1、在甲醇和水的混合体系中,通过芳醛,丙二腈和脂肪胺的三组分反应我们顺利得到了一系列多取代的吡啶和1,4-二氢吡啶衍生物。脂肪胺的结构对产物有很大的影响。所有产物的结构都通过IR、NMR、LC-MS等方法的鉴定,并用单晶衍射方法测定了其中1个吡啶衍生物的单晶结构。
2、以DABCO做碱,通过芳醛与环己二酮衍生物包括1,3-环己二酮和5,5-二甲基-1,3-环己二酮的一锅煮反应我们顺利得到了一系列呋喃,吡喃衍生物。同样所有的化合物也都经过了IR、NMR、LC-MS等方法的鉴定,并用单晶衍射方法测定了其中2个化合物的单晶结构。
3、通过乙酰基吡啶季铵盐,芳醛和丙二酸亚异丙酯或1,3-甲基巴比妥酸在室温搅拌下,以三乙胺为碱的多组分反应得到一系列未经报道的内盐化合物。所有化合物的结构都经过了IR、NMR、LC-MS的确证,并用单晶衍射方法测定了其中1个化合物的单晶结构。
Hetercyclics represent an important class of compounds for their biological activity and medical value. The synthesis of these compounds remains a hot topic of people’s attention. In recent years multicomponent reactions (MCRs) have been extensively studied for their simple procedures, efficiency and superior atom economy. This reaction which referred to as one-pot synthesis of three or more than three starting materials provides a powerful tool towards the rapid synthesis of diverse and complex heterocyclic compounds. In this work we developed a series of multicomponent reactions for synthesis of hetercyclic compounds and obtained some interesting results.
1. Polysubstituted pyridines and 1,4-dihydropyridines were prepared in a three-component reaction of aromatic aldehyde, malononitrile and aliphatic amine in a mixed solvent of methanol and water. The structures of amine play a determining factor for the formation of different products. All products were characterized by IR, 1H NMR, 13 CNMR, LC-MS spectroscopy. The single crystal structure of one polysubstituted pyridine was determined by X-ray diffraction method.
2. A series of furans or pyrans as well as some tetraketones were synthesized via one-pot reaction of aromatic aldehydes with 5,5-dimethylcyclohexane-1,3-dione and cyclohexane-1,3-dione in the presence of 1,4-Diazabicyclo[2.2.2]octane (DABCO). All the products were characterized by IR, 1H NMR, 13 CNMR, LC-MS spectroscopy. The single crystal structures of two products were determined by X-ray diffraction method.
3. The interesting zwitterionic compounds were synthesized by the multicomponent reactions of N-pyridylacetyl pyridinium salt, aromatic aldehydes, Medrum acid or 1, 3-dimethylbarbituric acid at room temperature using triethylamine as base catalyst. All the products were characterized by IR, 1H NMR, 13 CNMR, LC-MS spectroscopy. The single crystal structure of one representative zwitterionic salt was determined by X-ray diffraction method.
引文
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