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5-羟基-6-甲氧基-2-苄基-3,4-二氢异喹啉-1-酮的合成 被引量：1

Synthesis of 2-benzyl-5-hydroxy-6-methoxy-3,4-dihydroisoquinolin-1(2H)-one
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摘要 目的研究5-羟基-6-甲氧基-3,4-二氢异喹啉-1-酮衍生物的合成方法。方法以异香草酸甲酯为原料,通过烯丙基醚化、Claisen重排、氧化、西佛碱的制备、还原、分子内酯的胺解6步反应合成了5-羟基-6-甲氧基-2-苄基-3,4-二氢异喹啉-1-酮(1),总收率达55.0%。Schiff碱的制备、还原、酯的胺解3步在"一锅"内完成。结果合成了新的3,4-二氢异喹啉-1-酮衍生物,其结构经IR和1HNMR确认。结论设计的合成路线具有反应条件温和、操作简便、反应总收率高等优点。 Objective To investigate a new method of synthesis of 2-benzyl-5-hydroxyl-3, 4-dihydroisoquinolin-1 （2H）-one. Method 2-benzyl-5-hydroxy-6-methoxy-3,4-dihydro- isoquinolin-1 （2H）-one （1） was synthesized from methyl 3-hydroxy-4-methoxybenzoate via allyl etherification, Claisen rearrangement, oxidation, reductive amination and amidation. Reductive amintion and aminolysis were completed in one-pot. Results A new derivative of 3,4-dihydro- isoquinolin-1 （2H）-one was synthesized and its structure was identified by IR and 1HNMR. Conclusion The designed synthetic route was mild and simple in operation with higher yield.
作者 祝丽永 程彬 张三奇 陈战国
机构地区 陕西师范大学化学与材料科学学院 西安交通大学医学院药物研究所
出处 《西北药学杂志》 CAS 2008年第2期104-105,共2页 Northwest Pharmaceutical Journal
关键词 二氢异喹啉酮衍生物 CLAISEN重排 一锅法 3,4-Dihydroisoquinolin-1（2H）-one Claisen rearrangement One-Pot method
分类号 R914.5 [医药卫生—药物化学]
  • 相关文献

参考文献10

  • 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.
  • 2Banik BK, Manilas MS, Raju VS, et al. Tetracyclic isoquinolones and quinazolones via aryl radical cyclizations [J]. Heterocycles, 1998, 47(2) :639-642.
  • 3Jeong IY, Nagao Y. Novel synthesis of 4-oxo-1-isoquinolone derivatives utilizing inter and intramecular tandem carbopalladation-heteroeyclic ring expansion[J]. Tetrahedron Lett, 1998, 39..8677.
  • 4Dietrich A, Volmer A, Mansoori B, et al. Study of 4- Quinolone Antibiotics in Biological Samples by Short- Column Liquid Chromatography Coupled with Electrospray Ionization Tandem Mass Spectrometry[J]. Analytical Chem, 1997, 69(20):4143-4155.
  • 5Effland RC, Davis L, Hahn HG, et al. Synthesis of new dihydrooxathiino[ 2, 3-b] quinoline [J]. J. Heterocyclic Chem, 1996, 33(6):2055-2057.
  • 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.
  • 8任眉,张睿,徐云根,华维一.5-羟基-3,4-二氢异喹啉-1-酮的合成[J].合成化学,2006,14(5):532-533. 被引量：1
  • 9Tan WF, Wei DZ,Li YL. First total synthesis of (+)- glyflavanone-A [J]. Synthetic Communications, 2002, 32(7) :1077-1083.
  • 10Clive 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.

二级参考文献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.
  • 2M L Fein,E M Filachione.N-substituted lactamides[J].J Am Chem Soc,1953:2095-2097.
  • 3V Georgian,R J Harrisson,L L Skaletzky.The Synthesis of 5-oxoperhydroisoquinolines[J].J Org Chem,1962:4575-4579.
  • 4M J Suto,W R Turner,C M Arundel-Suto,et al.Dihydroisoquinolinones:The design and synthesis of a new series of potent inhibitors of poly(ADP-ribose) polymerase[J].Anti-Cancer Drug Design,1991,7:107-117.
  • 5H D Hollis Showalter,Anthony D Sercel,Michael A Stier,et al.Synthesis of 3,4-dihydro-1(2H)-isoquinolinones[J].J Heterocyclic Chem,2001,38:961.

同被引文献13

  • 1ChenN I J, Chang Y L, Teng C M, et al. Vasorelaxing and antioxidant constituents from Hemandia nym. p. haeifolia [ J ]. Planta Medica,2001,67(7) :593 - 598.
  • 2Roberto P, Emidio C, Gabriele C, et al. On the way to selective PARP-2 inhibitors. Design, synthesis, and preliminary evaluation of a series of isoquinolinone derivatives[J]. Chem Med Chem,2008,3(6):914-923.
  • 3Vikharev Y B, Shklyaev Y V, Anikina L V, et al. Synthesis and antl-inflammatory and analgesic activity of 2H-3,3-dimethyl-3,4-dihydroisoquinolin-1-ones [ J ]. Pharm Chem J,2005,39(8) :405 -408.
  • 4Poth J, Madoux F, Hodderb P, et al. Synthesis of small molecule inhibitors of the orphan nuclear receptor steroidogen/c factor-1 ( NRSA1 ) based on isoquinolinone scaffolds [ J ]. Bioorg Med Chem Lett, 2008,18 (8) :2628 - 2632.
  • 5Ni Y, Krelmak V, Lebl M. New approach for preparation of 2,3,7-trisubstituted 3,4-dihydroisoquinolinone libraries on solid phase[ J]. Molecular Diversity,2000, 5(3) :153 -161.
  • 6Ng P Y, Tang Y, Knosp W M, et al. Synthesis of diverse lactam carboxamides leading to the discovery of a new transcription-factor inhibitor[J]. Angew Chem Int Edit Engl,2007,46( 28 ) :5352 - 5355.
  • 7Li Q, Zhang S Q, Wang S C, et al. Efficient synthesis of thalifoline and its analogs[ J]. Synthetic Communications,2009,39(10) : 1752 - 1758.
  • 8Srcedhar E, Kumar R, Reddy G V, et al. The first total synthesis of neohelmanticins A-D amino derivatives of the 1,2-dihydroxypropane core and biological evaluation [ J ]. Tetrahedron: Asymmetry, 2009, 20 (4) :440 -448.
  • 9Showalter H D H, Sercel A D, Stier M A, et al. Synthesis of 3,4-dihydro-1 (2H) -isoquinolinones [ J ]. J HEeterocy Chem,2001,38 (4) :961 - 964.
  • 10Torisawa Y, Ake S, Minamikawa. Conversion of indanone oximes into isocarbostyrils [ J ]. J Bioorg Med Chem Lett, 2007,17 (2) : 453 - 455.

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西北药学杂志
2008年 第2期

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