Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 5
872
Views
20
CrossRef citations to date
0
Altmetric
Original Articles

A Practical Two‐Step Synthesis of 3‐Alkyl‐2,3‐dihydro‐1H‐isoindolin‐1‐ones

, , , &
Pages 853-861 | Received 21 Aug 2003, Published online: 20 Aug 2006

References

  • Belliotti , T. R. , Brink , W. A. and Kesten , S. R. 1998 . Isoindolinone enantiomers having affinity for the dopamine D‐4 receptor . Bioorg. Med. Chem. Lett. , 8 : 1499 [PUBMED] [INFOTRIEVE] [CSA]
  • Wada , T. and Fukuda , N. 1991 . Pharmacological profile of a new anxiolytic, DN‐2327, effect of ro15‐1788 and interaction with diazepam in rodents . Psychopharmacology , 103 : 314 [PUBMED] [INFOTRIEVE]
  • Fuchs , J. R. and Funk , R. L. 2001 . Total synthesis of (+/−)‐lennoxamine and (+/−)‐aphanorphine by intramolecular electrophilic aroamatic substitution reaction of 2‐amidoacroleins . Org. Lett. , 3 : 3923 (and references cited therein)[PUBMED] [INFOTRIEVE] [CSA] [CROSSREF]
  • Oppolzer , W. , Wills , M. , Kelly , M. J. , Signer , M. and Blagg , J. 1990 . Chiral toulene‐2, β‐sultam auxiliaries: asymmetric Diels‐Alder reactions of N‐enoyl derivatives . Tetrahedron Lett. , 31 : 5015 [CROSSREF]
  • Luzzio , F. A. and Zacherl , D. P. 1998 . Alkylation and annulation of 3‐(phenylsulfonyl)‐2‐alkyl‐2,3‐dihydroisoindol‐1‐ones . Tetrahedron Lett. , 39 : 2285 [CROSSREF]
  • Koseki , Y. , Kusano , S. , Sakata , H. and Nagasaka , T. 1999 . A new approach to isoindolobenzazepines via a ring‐expansion of isoindolisoquinoline: synthesis of lennoxamine and chilenine . Tetrahedron Lett. , 40 : 2169 [CROSSREF]
  • Hunter , R. and Richards , P. 2000 . Stereoselective tetrahydropyrido[2,1‐a]isoindolone synthesis via carbaionic and radical intermediates: a model study for the Tacaman alkaloid D/E ring fusion . Tetrahedron Lett. , 41 : 3755 [CROSSREF]
  • Kundu , N. G. and Khan , M. W. 2000 . Palladium‐catalysed heteroannulaion with terminal alkynes: a highly regio‐and stereoselective synthesis of (Z)‐3‐aryl(alkyl)idene isoindolin‐1‐ones . Tetrahedron , 56 : 4777 [CROSSREF]
  • Epsztajn , J. , Jozwiak , A. , Koluda , P. , Sadokierska , I. and Wilkowska , I. D. 2000 . Application of organolithium and related reagents in synthesis. Part 23: Synthetic strategies based on ortho‐aromatic metallation. Synthesis of 4b‐arylisondolo[2,1‐a]quinoline derivatives . Tetrahedron , 56 : 4837 [CROSSREF]
  • Hoarau , C. , Couture , A. , Deniau , E. and Grandclaudon , P. 2000 . A versatile synthesis of poly‐ and diversely substituted isoindolin‐1‐ones . Synthesis , : 655 [CROSSREF]
  • Couture , A. , Deniau , E. , Jonescu , D. and Grandclaudon , P. 1998 . LDA‐induced metalation of isoindolinones. An efficient route to 3‐substituted isoindoline derivatives . Tetrahedron Lett. , 39 : 2319 [CROSSREF]
  • Deniau , E. and Enders , D. 2001 . Synthesis of 3‐alkyl‐1‐isoindolines by alkylation of a benzotriazolyl substituted N‐dimethylamino‐phthalimidine . Tetrahedron , 57 : 2581 [CROSSREF]
  • Pérard‐Viret , J. , Prangé , T. , Tomas , A. and Royer , J. 2002 . A simple and efficient aysmmetric synthesis of 3‐alkyl‐isoindolin‐1‐ones . Tetrahedron , 58 : 5103 [CROSSREF]
  • Ukaji , Y. , Tsukamoto , K. , Nasada , Y. , Shimizu , M. and Fujisawa , T. 1993 . Regulation of diastereofacial selection in the allylation reaction of N‐acyliminium utilizing Lewis‐acids . Chem. Lett. , : 221
  • Campbell , J. B. , Dedinas , R. F. and Trumbower‐Walsh , S. A. 1996 . Addition of transiently‐generated methyl o‐lithiobenzanate to imines. An isoindolone annulation . J. Org. Chem. , 61 : 6205 [PUBMED] [INFOTRIEVE] [CROSSREF]
  • Enders , D. , Braig , V. and Raabe , G.A. 2001 . Asymmetric synthesis of 3‐aryl‐substituted 2,3‐dihydro‐1H‐isoindol‐1‐ones . Can. J. Chem. , 79 : 1528 [CROSSREF]
  • Deniau , E. and Enders , D. 2000 . A new simple and convenient synthesis of 3‐substituted phthalimidines . Tetrahedron Lett. , 41 : 2347 [CROSSREF]
  • Wang , E. C. , Chen , H. F. , Feng , P. K. , Lin , Y. L. and Hsu , M. K. 2002 . A new synthesis of 3‐alkyl‐isoindolinones . Tetrahedron Lett. , 43 : 9163 [CROSSREF]
  • Huang , P.‐Q. , Wang , S.‐L. , Ye , J.‐L. , Ruan , Y.‐P. , Huang , Y.‐Q. and Zheng , H. 1998 . An easy access to protected (4S,5R)‐5 alkyl‐4‐hydroxy‐2‐pyrrolidines and their use as versatile synthetic intermediates . Tetrahedron , 54 : 12547 [CROSSREF]
  • Huang , P.‐Q. , Chen , Q. F. , Chen , C.‐L. and Zhang , H.‐K. 1999 . Asymmetric synthesis of (−)‐(R)‐pyrrolam A starting from (S)‐malic acid . Tetrahedron: Asymmetry , 10 : 3827 [CROSSREF]
  • Chen , M.‐D. , He , M.‐Z. , Ruan , Y.‐P. and Huang , P.‐Q. 2002 . A versatile approach for the asymmetric synthesis of 3‐alkyl‐isoindolin‐1‐ones . Chin. J. Chem. , 20 : 1149
  • Kursanov , D. N. , Parnes , Z. N. and Loim , N. M. 1974 . Applications of ionic hydrogenation to organic synthesis . Synthesis , : 633 [CROSSREF]
  • Flitsch , von W. 1965 . Zur umsetzung cyclischer imid mit allylmagnesiumbromid Liebigs 3‐Formylmethylenepthalimidines . Ann. Chem. , 648 : 141
  • Mueller , H. R. and Seefelder , M. 1969 . Liebigs Ann. Chem. , 728 : 88
  • Nishio , T. and Yamamoto , H. 1995 . Preparation of 3‐hydroxyisoindolin‐1‐ones and O‐acylbenzamides, a study of ring–chain tautomerism . J. Heterocyclic Chem. , 32 : 883
  • Pigeon , P. and Decroix , B. 1996 . Benzothienoindolizidines via intramolecular aryl radical cyclization or palladium catalyzed cyclization . Tetrahedron Lett. , 37 : 7707 [CROSSREF]
  • Beis , C. 1904 . C. R. Acad. Sci., Paris , 138 : 988
  • Beis , C. 1904 . C. R. Acad. Sci., Paris , 139 : 62
  • Kato , Y. , Takemoto , M. and Achiwa , K. 1993 . Prostanoids and related‐compounds 6. Synthesis of isoindolinone derivatives possesing inhibitory activity for thromboxane‐A (2) analog (U‐46619)‐induced vasoconstriction . Chem. Pharm. Bull. , 41 : 2003 [PUBMED] [INFOTRIEVE] [CSA]
  • Aeberli , P. and Houlihan , W. J. 1968 . The lithuium aluminum hydride reduction products from heterocycles containing an isoindolone nucleus . J. Org. Chem. , 34 : 1720
  • Helberger , von J. H. and Hevér , D. B. 1938 . Uber die bildung von tetrabenzoporphin aus isoindolderivativaten . Justus Liebigs Ann. Chem. , 536 : 173
  • Bromberg , B. 1896 . Chem. Ber. , 29 : 1436
  • Wöelbling , B. 1905 . Chem. Ber. , 38 : 3925
  • Rosenthal , A. , Astbury , R. F. and Hubscher , A. 1958 . Reaction of aromatic ketoximes with carbon monoxide hydrogen . J. Org. Chem. , 23 : 1037
  • Bhatt , M. V. and Ravindranathan , M. 1973 . Aspects of tautomerism 5. Solvent, substituents, and steric effects in their ring‐chain tautomerism of ortho‐benzoylbenzamides . J. Chem. Soc. Perkin Trans II , : 1160 [CROSSREF]
  • Bartfeld , H. D. , Flitsch , W. and Gurke , K. 1974 . Acyliminium 3. Reaction of acyliminium salts with Grignard‐reagents . Chem. Ber. , 107 : 189

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.