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以1,2,3,4-四氢异喹啉为原料,先依次与二碳酸二叔丁酯、亚氯酸钠反应得到N-Boc-1,2,3,4-四氢-1-异喹啉酮,再和芳基格氏试剂反应得到分子内不对称还原胺化反应的底物,最后以ax-Josiphos为手性配体,[Ir(COD)Cl]2为金属前体,在Ti(OiPr)4和40%HBr溶液组成的催化体系中合成了8个手性1-芳基四氢异喹啉类化合物,其结构经1H NMR和13C NMR表征。该路线提供了一种以廉价1,2,3,4-四氢异喹啉为原料高效合成手性1-芳基四氢异喹啉类衍生物的新方法,为索利那新等药物的合成提供了新路径。
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通过环己二酮与β-二腈基苯乙烯的Michael加成得到2-氨基-3-氰基-4-芳基-5-氧代-1,4,5,6,7,8-六氢喹啉(1); 4-苯基六氢喹啉(1a)与环己二酮发生胺的加成缩合反应生成2-N-(3-氧代-1-环己烯基)氨基-3-氰基-4-苯基-5-氧代-1,4,5,6,7,8-六氢喹啉(2), 在碱性和氯化亚铜催化下进一步环合成4-苯基-5-氨基-二-(2-氧代环己烷)并[b,g]-1,3-二氢萘啶(3). 芳醛、α-萘胺和环己二酮在乙醇中共回流, 则一锅法完成9-芳基-5,6,7,8,9,10-六氢苯并[c]吖啶酮(4)的合成. 对合成中所涉及的化学反应机理进行了尝试性的讨论. 新化合物1a~4c均经IR, 1H NMR 及元素分析证明其结构. 相似文献
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本文报道了以(E)-1-(2-对甲苯磺酰胺基)-3-芳基丙-2-烯-1-酮(1)为底物与N-硫代丁二酰亚胺(2)通过亲电环化反应合成2-芳基-3-硫代-2,3-二氢喹啉-4(1H)-酮类化合物。以三氟化硼乙醚为催化剂(20 mol %),1,2-二氯乙烷为溶剂,反应温度为60 oC,可以60-92%的收率得到一系列2-芳基-3-硫代-4(1H)-喹啉酮衍生物,化合物3a-k均未见文献报道,其结构均经过1H NMR, 13C NMR以及高分辨质谱进行确定。 相似文献
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Indoprofen类似物的合成和表征 总被引:1,自引:0,他引:1
以邻硝基苯甲醛为超始原料,合成2-溴甲基-3-喹啉酸乙酯中间体,其分别与 苯胺、2-氯代苯胺、3-氯代苯胺、2-甲基苯胺和3-甲基苯胺发生Williamson反应, Williamson反应产物经闭环反应,得到新化合物2,3-二氢-1-氧代-2-苯基-1H-吡 咯并[3,4-b]喹啉(4a),2,3-二氢-1-氧代-2-(2-氯代苯基)-1H-吡咯并[3, 4-b]喹啉(4b),2,3-二氢-1-氧代-2-(3-氯代苯基)-1H-吡咯并[3,4-b]喹啉( 4c),2,3-二氢-1-氧代-2-(2-甲基苯基)-1H-吡咯并[3,4-b]喹啉(4d)和2, 3-二氢-1-氧代-2-(3-甲基苯基)-1H-吡咯并[3,4-b]喹啉(4e)。12个新化合物 由元素分析、红外光谱、核磁共振氢谱、质谱予以证实。 相似文献
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3-Allenyl-4-aryl-7,7-dimethyl-5-oxo-2-thioxo-1,2,3,4,5,6,7,8-octahydroquinoline-3-carbonitriles were synthesized via [3,3]-sigmatropic
rearrangement of 4-aryl-7,7-dimethyl-5-oxo-2-(prop-2-yn-1-ylsulfanyl)-1,4,5,6,7,8-hexahydroquinoline-3-carbonitriles. The
structure of 3-allenyl-7,7-dimethyl-4-(2-nitrophenyl)-5-oxo-2-thioxo-1,2,3,4,5,6,7,8-octahydroquinolin-3-carbonitrile was
determined by X-ray analysis. 相似文献
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Xue-Mei Wang He-Lin Ye Zheng-Jun Qaun Xi-Cun Wang 《Research on Chemical Intermediates》2013,39(6):2357-2367
A series of 1-aryl-1,2-dihydrobenzo[f]quinolin-3(4H)-one derivatives and 4-aryl-7,7-dimethyl-5-oxo-3,4,5,6,7,8-hexahydrocoumarin derivatives have been synthesized by one-pot multicomponent reaction of Meldrum’s acid with benzaldehyde, naphthalene-2-amine, or cyclohexanedione in PEG-400. The method has the advantages of mild reaction conditions, good yields, and easy processing, and is environmentally benign. 相似文献
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Jairo Quiroga Braulio Insuasty Angelina Hormaza Claudio Saitz Carolina Jullian 《Journal of heterocyclic chemistry》1998,35(3):575-578
Reaction of 5-amino-3-methyl-1-phenylpyrazole ( 1a ) and 5-amino-3-(4-chlorophenyl)-1H-pyrazole ( 1b ) with dimedone ( 2 ) and p-susbstituted benzaldehydes 3 in ethanol, afforded in all cases tricyclic linear 4-aryl-7,7-dimethyl-4,7,8,9-tetrahydro-6H-pyrazolo[3,4-b]quinolin-5-ones ( 4a-j ) in good yields. The linear structures and hence the regiospecificity of the reaction were established by nmr measurements. 相似文献
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K. F. Turchin A. D. Yanina T. Ya. Filipenko E. E. Mikhlina Yu. N. Sheinker L. N. Yakhontov 《Chemistry of Heterocyclic Compounds》1985,21(9):1039-1048
It was shown by means of 1H and 13C NMR spectroscopy that the reaction of 2-arylmethylene-3-oxoquinuclidines with hydrazine hydrate gives 4a-hydroxy-7-aryl-4a,5,7,7a-tetrahydropyrazolo[4,3-b]quinuclidines, which are stable in the crystalline state but undergo dehydration to the corresponding 7-aryl-6H-7,7a-dihydropyrazolo[4,3-b]quinuclidines in solutions. The latter undergo cleavage to 3-(4-piperidyl)-5-arylpyrazoles when they are heated in an alkaline medium.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1248–1256, September, 1985. 相似文献