3-苄基-4-(4-氯苯基)-3,7-二氢-5H-异苯并呋喃并[5,6-d]咪唑-5-酮的合成及结构表征
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摘要
以4-咪唑丙烯酸为原料,经过酯化、N烷基化、还原、缩合、D-A成环、芳香化等一系列的反应合成3-苄基-4-(4-氯苯基)-3,7-二氢-5H-异苯并呋喃并[5,6-d]咪唑-5-酮.目标化合物的结构经1H NMR和LC-MS确证.
3-Benzyl-4-( 4-chlorophenyl)-3,7-dihydro-5 H-isobenzofuro[5,6-d]imidazol-5-one was synthesized from( E)-3-( 4-chlorophenyl) acrylic acid by esterification,N-alkylation,reduction,condensation,Diels-Alder cyclization,and aromatization. Its structure was characterized and confirmed by ~1H NMR and LC-MS results.
3-Benzyl-4-( 4-chlorophenyl)-3,7-dihydro-5 H-isobenzofuro[5,6-d]imidazol-5-one was synthesized from( E)-3-( 4-chlorophenyl) acrylic acid by esterification,N-alkylation,reduction,condensation,Diels-Alder cyclization,and aromatization. Its structure was characterized and confirmed by ~1H NMR and LC-MS results.
引文
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[2]FU X,SCHMITZ F J,TANNER R S,et al.New imidazole alkaloids and zinc complexes from micronesian sponge Leucetta cf.chagosensis[J].J Nat Prod,1998,61(3):384-386.
[3]HASSAN W,EDRADA R,EBEL R,et al.New imidazole alkaloids from the indonesian sponge Leucetta chagosensis[J].J Nat Prod,2004,67(5):817-822.
[4]KOSWATTA P B,LOVELY C J.Structure and synthesis of 2-aminoimidazole alkaloids from Leucetta and Clathrina sponges[J].Nat Prod Rep,2010,28(3):511-528.
[5]ZHONG J.Muscarine,imidaozle,oxazole and thiazole alkaloids[J].Nat Prod Rep,2013,30(6):869-915.
[6]宫凯凯.三种海洋生物化学成分及生物活性研究[D].青岛:中国海洋大学,2014.
[7]GONG K K,XU-LI T,GANG Z.Polyhydroxylated steroids from the South China Sea soft coral Sarcophyton sp.and their cytotoxic and antiviral activities[J].Mar Drugs,2013,11(12):4788-4798.
[8]GIBBONS J B,GLIGORICH K M,WELM B E,et al.Synthesis of the reported structures for kealiinines B and C[J].Org Lett,2012,14(18):4734-4737.
[9]DAS J,BHAN A,MANDAL S S,et al.Total syntheses and cytotoxicity of kealiiquinone,2-deoxy-2-aminokealiiquinone and analogs[J].Bioorg Med Chem Lett,2013,23(22):6183-6187.
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[12]LOVELY C J,RASAPALLI S,MUKHERJEE S,et al.Efficient preparation of urocanic acid derivatives from histidine[J].Heterocycles,2010,80(2):1353-1358.
[13]LOVELY C J,DU H,SIVAPPA R,et al.Preparation and Diels-Alder chemistry of 4-vinylimidazoles[J].J Org Chem,2007,72(10):3741-3749.
[14]NIELAND N P R,RENNISON D,BROADBEAR J H,et al.14β-arylpropiolylamino-17-cyclopropyl-methyl-7,8-dihydronormorphinones and related opioids.Further examples of pseudoirreversibleμopioid receptor antagonists[J].J Med Chem,2009,52(21):6926-6930.