Simple Synthesis of 4‐Substituted 1(2H)‐Isoquinolinones via Electrophilic Trapping of Lithiated Mono‐ and Dianion Precursors

References

• Peukert , S. and Schwahn , U. 2004 . New inhibitors of poly(ADP‐ribose) polymerase (PARP) . Expert Opin. Therapeu. Pat. , 14 : 1531 – 1551 . Recent reviews on PARP‐1 inhibitors
   Web of Science ®Google Scholar
• Woon , E. C. Y. and Threadgill , M. D. 2005 . Poly(ADP‐ribose)polymerase inhibition—where now? . Curr. Med. Chem. , 12 : 2373 – 2392 .
   PubMedGoogle Scholar
• Suto , M. J. , Turner , W. R. and Werbel , L. M. Preparation of substituted dihydroisoquinolinones and related compounds as radiation therapy potentiators and chemotherapeutic agents . Eur. Pat. Appl. 355750 . 1990 . Chem. Abstr., 113, 132025
   Google Scholar
• Showalter , H. D. H. , Sercel , A. D. , Stier , M. A. and Turner , W. A. 2001 . Synthesis of 3,4‐dihydro‐1(2H)‐isoquinolinones . J. Heterocycl. Chem. , 38 : 961 – 964 .
   Google Scholar
• Alvarez , M. and Joule , J. A. 2005 . Product class 6: Isoquinolinones . Sci. Synth. , 15 : 839 – 906 . Recent reviews
   Google Scholar
• Glushkov , V. A. and Shklyaev , Y. V. 2001 . Synthesis of 1(2H)‐isoquinolones . Chem. Heterocycl. Compd. , 37 : 663 – 687 .
   Google Scholar
• Muchowski , J. M. , Horning , D. E. and Lacasse , G. 1971 . Isocarbostyrils: I. electrophilic substitution reactions . Can. J. Chem. , 49 : 2785 – 2796 .
   Google Scholar
• Muchowski , J. M. , Horning , D. E. and Lacasse , G. 1971 . Isocarbostyrils, II: conversion of 2‐methyl‐4‐acyl‐5‐nitroisocarbostyrils to 2‐substituted indole‐4‐carboxylic acids . Can. J. Chem. , 49 : 2797 – 2802 .
   Google Scholar
• Nuvole , A. and Pinna , G. A. 1978 . Synthesis of 1‐amino‐4‐chloroisoquinoline: a new approach to 1‐aminoisoquinoline . J. Heterocycl. Chem. , 15 : 1513 – 1514 .
   Google Scholar
• Fujio , M. , Satoh , H. , Matsumoto , T. and Futamura , T. Preparation of 4‐piperidinyl‐1‐ isoquinolinone derivatives as polyadenosine diphosphoribose polymerase inhibitors for treatment of cerebral infarction . PCT Intl. Appl. WO 2005/113540 . 2005 . Chem. Abstr., 144, 22822
   Google Scholar
• Asano , J. , Shiga , F. , Takano , Y. and Ishiyama , J. 4‐Aryl‐5‐hydroxyisoquinolinones, their preparation, and poly(ADP‐ribose) polymerase inhibitors containing them . Jpn. Pat. Appl. 2004/043458 . 2004 . Chem. Abstr., 140 157492
   Google Scholar
• Robison , M. M. and Robison , B. L. 1958 . Reaction of 1‐chloroisoquinoline with peracetic acid . J. Org. Chem. , 23 : 1071 – 1072 .
   Google Scholar
• Shizuta , Y. , Ito , S. , Nakata , K. and Hayaishi , O. 1980 . Poly(ADP‐ribose) synthetase from calf thymus . Methods Enzymol. , 66 : 159 – 165 .
   PubMedGoogle Scholar
• Bender , S. L. , Bhumralkar , D. , Collins , M. R. , Cripps , S. J. , Deal , J. G. , Nambu , M. D. , Palmer , C. L. , Peng , Z. , Varney , M. D. and Jia , L. Synthesis of heteroarylbenzamides and analogs used for inhibiting protein kinases . PCT Int. Appl. WO 2001/053274 . 2001 . Chem. Abstr., 135, 137516
   Google Scholar
• Lee , W.‐C. , Sun , L. , Shan , F. , Chuaqui , C. , Cornebise , M. , Pontz , T. W. , Carter , M. , Singh , J. , Boriack‐Sjodin , P. A. , Ling , L. and Petter , R. C. Preparation of 2‐pyrazolylpyridine derivatives as TGFβ receptor inhibitors . PCT Int. Appl. WO 2004/072033 . 2004 . Chem. Abstr., 141, 225504
   Google Scholar
• Bold , G. and Manley , P. W. Preparation of isoquinolinamines inhibiting angiogenesis and/or VEGF receptor tyrosine kinase . PCT Int. Appl. WO 2001/058899 . 2001 . Chem. Abstr., 135, 180710
   Google Scholar
• Kimura , M. , Waki , I. , Deguchi , Y. , Amemiya , K. and Maeda , T. 1983 . 1(2H)‐Isoquinolones as potential antiallergic agents . Chem. Pharm. Bull. , 31 : 1277 – 1282 .
   PubMedGoogle Scholar
• Wang , X. A. , Sun , L.‐Q. , Sit , S.‐Y. , Sin , N. , Scola , P. M. , Hewawasam , P. , Good , A. C. , Chen , Y. and Campbell , J. A. Preparation of peptides as hepatitis C virus inhibitors . PCT Int. Appl. WO 2003/099274 . 2003 . Chem. Abstr., 140 , 16975
   Google Scholar