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5-羟基-3,4-二氢异喹啉-1-酮的合成 被引量:1

Synthesis of 3,4-Dihydro-5-hydroxy-1(2H)-isoquinolinone
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摘要 以异喹啉为起始原料,经成盐、磺化得异喹啉-5-磺酸(3),3与熔融的氢氧化钠和氢氧化钾反应得1,5-二羟基异喹啉(4),以5%Pd-C为催化剂还原4得5-羟基-3,4-二氢异喹啉-1-酮(1),总收率47.6%。1的结构经1H NMR和MS确证。 3,4-Dihydro-5-hydroxy-1 (2H) -isoquinolinone ( 1 ) was synthesized from isoquinoline (2) by a three-step reaction that isoquinoline-5-sulfonic acid(3) was prepared by the reaction of fuming sulfuric acid with 2, 1 ,5-dihydroxy-isoquinoline(4) was obtained from 3 in a melted mixture of sodium hydroxide and potassium hydroxide and hydrogenation of 4 to 1 was fulfilled in the presence of 5 % Pd-C. The overall yield of 1 was 47.6%. The structure of 1 was identified by ^1 H NMR and MS.
出处 《合成化学》 CAS CSCD 2006年第5期532-533,共2页 Chinese Journal of Synthetic Chemistry
关键词 异喹啉 喹啉酮 还原反应 合成 isoquinoline isoquinolinone reducing reaction synthesis
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参考文献5

  • 1Lberto Chiarugi,Elena Meli,Maura Calvani,et al.Novel isoquinolinone-derived Inhibitors of poly(ADP-ribose) polymerase-1:Pharmacological characterization and neurprotective effects in an in vitro model of cerebral ischemia[J].J Pharmacol Exp Ther,2003,305(3):943-949.
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同被引文献9

  • 1Davis FA, AndemichaYW. Sulfinimine mediated asymmeteic synthesis of 3-substituted-1 (2H)-isoquinolones: (3R, 4S)-( - )-4-hydroxy-3-phenyltetr ahydroisoquinoline[J]. Tetrahedron Lett, 1998, 39:3099.
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  • 6Lberto Chiarugi, Elena Meli, Maura Calvani, et al. Novel isoquinolinone-derived inhibitors of poly (ADP-ribose) polymerase-1.. Pharmacological characterization and neurprotective effects in an in vitro model of cerebral ischemia [J]. J Pharmacol Exp Ther, 2003, 305(3) 1943-949.
  • 7Miyake, Yoshinori SH, Hashimoto N, et al. Yoshinori Synthesis of 3, 4-dihydro-5-[llC]methoxy-l(2H)-isoquinolinone as a potential tracer for poly(ADP-ribose) synthetase[J]. Journal of Labelled Compounds & Radiopharmaceuticals, 2000, 43 (10) : 983-988.
  • 8Tan WF, Wei DZ,Li YL. First total synthesis of (+)- glyflavanone-A [J]. Synthetic Communications, 2002, 32(7) :1077-1083.
  • 9Clive DLJ, Yu M, Sannigrahi M. Synthesis of Optically Pure (+)-Puraquinonic Acid and Assignment of Absolute Configuration to Natural (-)-Puraquinonic Acid. Use of Radical Cyclization for Asymmetric Generation of a Quaternary Center [J]. J Org Chem, 2004, 69(12) :4116-4125.

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