8-取代喹哪啶的合成与晶体结构

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8-取代喹哪啶的合成与晶体结构

作者：吴天泉王健华沈芳胡艾希

来源：《湖南大学学报·自然科学版》2010年第01期

摘要: 2-取代苯胺与巴豆醛反应合成了5种8-取代喹哪啶。讨论了反应因素对反应的影响,得到了较好的结果。8-取代喹哪啶的结构经1HNMR和MS分析确证,并用单晶X-射线衍射测

定了化合物Ⅰa和Ⅰb的晶体结构。化合物Ⅰa晶体属正交晶系,空间群为Pca21,晶胞参数为:a = 1.27961(9) nm, b = 0.50660(4) nm, c = 1.31181(9) nm, Z = 4,V = 850.38(11) nm3, Dx = 1.387g/cm3, F(000)= 368, R1 = 0.0288, ωR2 = 0.0731,S = 1.01;化合物Ⅰb晶体属单斜晶系,空间群为P21/c晶

胞参数为:a = 0.50440(17) nm, b = 1.3467(4) nm, c = 1.3391(4) nm, β = 97.678(4)°;Z = 4,V =

901.4(5) nm3, Dx = 1.636g/cm3,F(000)= 440, R1 = 0.0711, ωR2 = 0.1951,S = 1.09。选择合适溶剂和添加剂,反应收率较文献值有较大提高。

关键词 :8-取代喹哪啶;合成;晶体结构

中图分类号:TQ 253. 23文献标识码:A

Synthesis and Crystal structure of 8-Substitued Quinaldine

Wu Tian-Quan, Wang Jian-Hua, Shen Fang and Hu Ai-Xi *

(1 College of Chemistry and Chemical Engineering, Hunan Univ,410082 Changsha, China;2 Department of biology technology&environment science, ChangSha College, changsha, 410003)

Abstract: Five quinaldine derivatives were synthesized through the reaction of 2-substituted aniline and crotonaldehyde. We were investigated the effect of conditions on reaction. Their structure confirmed by 1HNMR and MS. Crystal structure of Ⅰa and Ⅰb have been determined by X-ray diffraction, The compound Ⅰa crystal belongs to orthorhombic system with space group Pca21 and cell parameters: a = 1.27961(9) nm, b = 0.50660(4)nm, c = 1.31181(9) nm, Z = 4,V = 850.38(11) nm3, Dx = 1.387 g/cm3, F(000)= 368, R1 = 0.0288, ωR2 = 0.0731,S = 1.01;The compound Ⅰb crystal belongs to monoclinic system with space group P21/c and cell parameters: a = 0.50440(17) nm,b = 13.467(4)nm, c = 13.391(4)nm, β = 97.678(4)°;Z = 4,V = 901.4(5) nm3, Dx = 1.636g/cm3,F(000) = 440, R1 = 0.0711, ωR2 = 0.1951,S = 1.09.The yields of 8-substituted quinaldine are higher than that

of literature by using appropriate slovent and additives.

Key words: 8-substitued quinaldine, synthesis, crystal structure

8-取代喹哪啶是一类重要的精细化工中间体[1~2],Dehnert等[3]以8-氨基喹哪啶为原料合成了颜料C.I P.Y138;Bray等[4]以8-卤代喹哪啶为原料合成了治疗疟疾的伯喹及氯喹类衍生