메뉴 건너뛰기




Volumn 34, Issue 5, 2004, Pages 853-861

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

Author keywords

Grignard reaction; Isoindolin 1 one; Phthalimide; Reductive alkylation

Indexed keywords

3 BENZYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; 3 ETHYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; 3 ISOBUTYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; 3 METHYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; 3 N BUTYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; 3 N HEPTYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; 3 N PENTYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; 3 N PROPYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; 3 PHENYL 2,3 DIHYDRO 1H ISOINDOLIN 1 ONE; ISOINDOLE DERIVATIVE; PHTHALIMIDE; UNCLASSIFIED DRUG;

EID: 1642321243     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120028358     Document Type: Article
Times cited : (19)

References (36)
  • 1
    • 0032537535 scopus 로고    scopus 로고
    • Isoindolinone enantiomers having affinity for the dopamine D-4 receptor
    • (a) Belliotti, T.R.; Brink, W.A.; Kesten, S.R. Isoindolinone enantiomers having affinity for the dopamine D-4 receptor. Bioorg. Med. Chem. Lett. 1998, 8, 1499;
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 1499
    • Belliotti, T.R.1    Brink, W.A.2    Kesten, S.R.3
  • 2
    • 0026079335 scopus 로고
    • Pharmacological profile of a new anxiolytic, DN-2327, effect of ro15-1788 and interaction with diazepam in rodents
    • (b) Wada, T.; Fukuda, N. Pharmacological profile of a new anxiolytic, DN-2327, effect of ro15-1788 and interaction with diazepam in rodents. Psychopharmacology 1991, 103, 314;
    • (1991) Psychopharmacology , vol.103 , pp. 314
    • Wada, T.1    Fukuda, N.2
  • 3
    • 0035969615 scopus 로고    scopus 로고
    • Total synthesis of (+/-)-lennoxamine and (+/-)-aphanorphine by intramolecular electrophilic aroamatic substitution reaction of 2-amidoacroleins
    • and references cited therein
    • (b) Fuchs, J.R.; Funk, R.L. Total synthesis of (+/-)-lennoxamine and (+/-)-aphanorphine by intramolecular electrophilic aroamatic substitution reaction of 2-amidoacroleins. Org. Lett. 2001, 3, 3923 (and references cited therein).
    • (2001) Org. Lett. , vol.3 , pp. 3923
    • Fuchs, J.R.1    Funk, R.L.2
  • 4
    • 0025158543 scopus 로고
    • Chiral toulene-2, β-sultam auxiliaries: Asymmetric Diels-Alder reactions of N-enoyl derivatives
    • (a) Oppolzer, W.; Wills, M.; Kelly, M.J.; Signer, M.; Blagg, J. Chiral toulene-2, β-sultam auxiliaries: asymmetric Diels-Alder reactions of N-enoyl derivatives. Tetrahedron Lett. 1990, 31, 5015;
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5015
    • Oppolzer, W.1    Wills, M.2    Kelly, M.J.3    Signer, M.4    Blagg, J.5
  • 5
    • 0032537151 scopus 로고    scopus 로고
    • Alkylation and annulation of 3-(phenylsulfonyl)-2-alkyl-2,3-dihydroisoindol-1-ones
    • (b) Luzzio, F.A.; Zacherl, D.P. Alkylation and annulation of 3-(phenylsulfonyl)-2-alkyl-2,3-dihydroisoindol-1-ones. Tetrahedron Lett. 1998, 39, 2285;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2285
    • Luzzio, F.A.1    Zacherl, D.P.2
  • 6
    • 0033548469 scopus 로고    scopus 로고
    • A new approach to isoindolobenzazepines via a ring-expansion of isoindolisoquinoline: Synthesis of lennoxamine and chilenine
    • (c) Koseki, Y.; Kusano, S.; Sakata, H.; Nagasaka, T. A new approach to isoindolobenzazepines via a ring-expansion of isoindolisoquinoline: synthesis of lennoxamine and chilenine. Tetrahedron Lett. 1999, 40, 2169;
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2169
    • Koseki, Y.1    Kusano, S.2    Sakata, H.3    Nagasaka, T.4
  • 7
    • 0034611975 scopus 로고    scopus 로고
    • Stereoselective tetrahydropyrido[2,1-a]isoindolone synthesis via carbaionic and radical intermediates: A model study for the Tacaman alkaloid D/ E ring fusion
    • (d) Hunter, R.; Richards, P. 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. 2000, 41, 3755;
    • (2000) Tetrahedron Lett. , vol.41 , pp. 3755
    • Hunter, R.1    Richards, P.2
  • 8
    • 0034733535 scopus 로고    scopus 로고
    • Palladium-catalysed hetero-annulaion with terminal alkynes: A highly regio-and stereoselective synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1-ones
    • (e) Kundu, N.G.; Khan, M.W. Palladium-catalysed hetero-annulaion with terminal alkynes: a highly regio-and stereoselective synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1-ones. Tetrahedron 2000, 56, 4777;
    • (2000) Tetrahedron , vol.56 , pp. 4777
    • Kundu, N.G.1    Khan, M.W.2
  • 9
    • 0342626647 scopus 로고    scopus 로고
    • 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
    • (f) Epsztajn, J.; Jozwiak, A.; Koluda, P.; Sadokierska, I.; Wilkowska, I.D. 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 2000, 56, 4837;
    • (2000) Tetrahedron , vol.56 , pp. 4837
    • Epsztajn, J.1    Jozwiak, A.2    Koluda, P.3    Sadokierska, I.4    Wilkowska, I.D.5
  • 10
    • 0034109057 scopus 로고    scopus 로고
    • A versatile synthesis of poly- and diversely substituted isoindolin-1-ones
    • (g) Hoarau, C.; Couture, A.; Deniau, E.; Grandclaudon, P. A versatile synthesis of poly- and diversely substituted isoindolin-1-ones. Synthesis 2000, 655.
    • (2000) Synthesis , pp. 655
    • Hoarau, C.1    Couture, A.2    Deniau, E.3    Grandclaudon, P.4
  • 11
    • 0032537204 scopus 로고    scopus 로고
    • LDA-induced metalation of isoindolinones. An efficient route to 3-substituted isoindoline derivatives
    • (a) Couture, A.; Deniau, E.; Jonescu, D.; Grandclaudon, P. LDA-induced metalation of isoindolinones. An efficient route to 3-substituted isoindoline derivatives. Tetrahedron Lett. 1998, 39, 2319;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2319
    • Couture, A.1    Deniau, E.2    Jonescu, D.3    Grandclaudon, P.4
  • 12
    • 0035953025 scopus 로고    scopus 로고
    • Synthesis of 3-alkyl-1-isoindolines by alkylation of a benzotriazolyl substituted N-dimethylamino-phthalimidine
    • (b) Deniau, E.; Enders, D. Synthesis of 3-alkyl-1-isoindolines by alkylation of a benzotriazolyl substituted N-dimethylamino-phthalimidine. Tetrahedron 2001, 57, 2581;
    • (2001) Tetrahedron , vol.57 , pp. 2581
    • Deniau, E.1    Enders, D.2
  • 13
    • 0037124518 scopus 로고    scopus 로고
    • A simple and efficient aysmmetric synthesis of 3-alkyl-isoindolin-1-ones
    • (c) Pérard-Viret, J.; Prangé, T.; Tomas, A.; Royer, J. A simple and efficient aysmmetric synthesis of 3-alkyl-isoindolin-1-ones. Tetrahedron 2002, 58, 5103.
    • (2002) Tetrahedron , vol.58 , pp. 5103
    • Pérard-Viret, J.1    Prangé, T.2    Tomas, A.3    Royer, J.4
  • 14
    • 0002736446 scopus 로고
    • Regulation of diastereofacial selection in the allylation reaction of N-acyliminium utilizing Lewis-acids
    • Ukaji, Y.; Tsukamoto, K.; Nasada, Y.; Shimizu, M.; Fujisawa, T. Regulation of diastereofacial selection in the allylation reaction of N-acyliminium utilizing Lewis-acids. Chem. Lett. 1993, 221.
    • (1993) Chem. Lett. , pp. 221
    • Ukaji, Y.1    Tsukamoto, K.2    Nasada, Y.3    Shimizu, M.4    Fujisawa, T.5
  • 15
    • 0000525743 scopus 로고    scopus 로고
    • Addition of transiently-generated methyl o-lithiobenzanate to imines. An isoindolone annulation
    • (a) Campbell, J.B.; Dedinas, R.F.; Trumbower-Walsh, S.A. Addition of transiently-generated methyl o-lithiobenzanate to imines. An isoindolone annulation. J. Org. Chem. 1996, 61, 6205;
    • (1996) J. Org. Chem. , vol.61 , pp. 6205
    • Campbell, J.B.1    Dedinas, R.F.2    Trumbower-Walsh, S.A.3
  • 16
    • 0035680653 scopus 로고    scopus 로고
    • Asymmetric synthesis of 3-aryl-substituted 2,3-dihydro-1H-isoindol-1-ones
    • (b) Enders, D.; Braig, V.; Raabe, G.A. Asymmetric synthesis of 3-aryl-substituted 2,3-dihydro-1H-isoindol-1-ones. Can. J. Chem. 2001, 79, 1528.
    • (2001) Can. J. Chem. , vol.79 , pp. 1528
    • Enders, D.1    Braig, V.2    Raabe, G.A.3
  • 17
    • 0034175586 scopus 로고    scopus 로고
    • A new simple and convenient synthesis of 3-substituted phthalimidines
    • (a) Deniau, E.; Enders, D. A new simple and convenient synthesis of 3-substituted phthalimidines. Tetrahedron Lett. 2000, 41, 2347;
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2347
    • Deniau, E.1    Enders, D.2
  • 19
    • 0032497681 scopus 로고    scopus 로고
    • An easy access to protected (4S,5R)-5 alkyl-4-hydroxy-2-pyrrolidines and their use as versatile synthetic intermediates
    • (a) Huang, P.-Q.; Wang, S.-L.; Ye, J.-L.; Ruan, Y.-P.; Huang, Y.-Q.; Zheng, H. An easy access to protected (4S,5R)-5 alkyl-4-hydroxy-2-pyrrolidines and their use as versatile synthetic intermediates. Tetrahedron 1998, 54, 12547;
    • (1998) Tetrahedron , vol.54 , pp. 12547
    • Huang, P.-Q.1    Wang, S.-L.2    Ye, J.-L.3    Ruan, Y.-P.4    Huang, Y.-Q.5    Zheng, H.6
  • 20
    • 0001037317 scopus 로고    scopus 로고
    • Asymmetric synthesis of (-)-(R)-pyrrolam A starting from (S)-malic acid
    • (b) Huang, P.-Q.; Chen, Q.F.; Chen, C.-L.; Zhang, H.-K. Asymmetric synthesis of (-)-(R)-pyrrolam A starting from (S)-malic acid. Tetrahedron: Asymmetry 1999, 10, 3827.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 3827
    • Huang, P.-Q.1    Chen, Q.F.2    Chen, C.-L.3    Zhang, H.-K.4
  • 21
    • 0742281412 scopus 로고    scopus 로고
    • A versatile approach for the asymmetric synthesis of 3-alkyl-isoindolin-1-ones
    • Chen, M.-D.; He, M.-Z.; Ruan, Y.-P.; Huang, P.-Q. A versatile approach for the asymmetric synthesis of 3-alkyl-isoindolin-1-ones. Chin. J. Chem. 2002, 20, 1149.
    • (2002) Chin. J. Chem. , vol.20 , pp. 1149
    • Chen, M.-D.1    He, M.-Z.2    Ruan, Y.-P.3    Huang, P.-Q.4
  • 22
    • 84989511047 scopus 로고
    • Applications of ionic hydrogenation to organic synthesis
    • Kursanov, D.N.; Parnes, Z.N.; Loim, N.M. Applications of ionic hydrogenation to organic synthesis. Synthesis 1974, 633.
    • (1974) Synthesis , pp. 633
    • Kursanov, D.N.1    Parnes, Z.N.2    Loim, N.M.3
  • 23
    • 84956248710 scopus 로고
    • Zur umsetzung cyclischer imid mit allylmagnesium-bromid Liebigs 3-Formylmethylenepthalimidines
    • (a) Flitsch, von W. Zur umsetzung cyclischer imid mit allylmagnesium-bromid Liebigs 3-Formylmethylenepthalimidines. Ann. Chem. 1965, 648, 141;
    • (1965) Ann. Chem. , vol.648 , pp. 141
    • Von Flitsch, W.1
  • 25
    • 84993858223 scopus 로고
    • Preparation of 3-hydroxyisoindolin-1-ones and O-acylbenzamides, a study of ring-chain tautomerism
    • (c) Nishio, T.; Yamamoto, H. Preparation of 3-hydroxyisoindolin-1-ones and O-acylbenzamides, a study of ring-chain tautomerism. J. Heterocyclic Chem. 1995, 32, 883;
    • (1995) J. Heterocyclic Chem. , vol.32 , pp. 883
    • Nishio, T.1    Yamamoto, H.2
  • 26
    • 0030597152 scopus 로고    scopus 로고
    • Benzothienoindolizidines via intramolecular aryl radical cyclization or palladium catalyzed cyclization
    • (d) Pigeon, P.; Decroix, B. Benzothienoindolizidines via intramolecular aryl radical cyclization or palladium catalyzed cyclization. Tetrahedron Lett. 1996, 37, 7707.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7707
    • Pigeon, P.1    Decroix, B.2
  • 29
    • 0027723305 scopus 로고
    • Prostanoids and related-compounds 6. Synthesis of isoindolinone derivatives possesing inhibitory activity for thromboxane-A (2) analog (U-46619)-induced vasoconstriction
    • (c) Kato, Y.; Takemoto, M.; Achiwa, K. Prostanoids and related-compounds 6. Synthesis of isoindolinone derivatives possesing inhibitory activity for thromboxane-A (2) analog (U-46619)-induced vasoconstriction. Chem. Pharm. Bull. 1993, 41, 2003.
    • (1993) Chem. Pharm. Bull. , vol.41 , pp. 2003
    • Kato, Y.1    Takemoto, M.2    Achiwa, K.3
  • 30
    • 0000581414 scopus 로고
    • The lithuium aluminum hydride reduction products from heterocycles containing an isoindolone nucleus
    • Aeberli, P.; Houlihan, W.J. The lithuium aluminum hydride reduction products from heterocycles containing an isoindolone nucleus. J. Org. Chem. 1968, 34, 1720.
    • (1968) J. Org. Chem. , vol.34 , pp. 1720
    • Aeberli, P.1    Houlihan, W.J.2
  • 31
    • 2042466850 scopus 로고
    • Uber die bildung von tetrabenzoporphin aus isoindolderivativaten
    • Helberger, von J.H.; Hevér, D.B. Uber die bildung von tetrabenzoporphin aus isoindolderivativaten. Justus Liebigs Ann. Chem. 1938, 536, 173.
    • (1938) Justus Liebigs Ann. Chem. , vol.536 , pp. 173
    • Von Helberger, J.H.1    Hevér, D.B.2
  • 34
    • 1642339218 scopus 로고
    • Reaction of aromatic ketoximes with carbon monoxide hydrogen
    • Rosenthal, A.; Astbury, R.F.; Hubscher, A. Reaction of aromatic ketoximes with carbon monoxide hydrogen. J. Org. Chem. 1958, 23, 1037.
    • (1958) J. Org. Chem. , vol.23 , pp. 1037
    • Rosenthal, A.1    Astbury, R.F.2    Hubscher, A.3
  • 35
    • 37049131422 scopus 로고
    • Aspects of tautomerism 5. Solvent, substituents, and steric effects in their ring-chain tautomerism of ortho-benzoylbenzamides
    • Bhatt, M.V.; Ravindranathan, M. Aspects of tautomerism 5. Solvent, substituents, and steric effects in their ring-chain tautomerism of ortho-benzoylbenzamides. J. Chem. Soc. Perkin Trans II 1973, 1160.
    • (1973) J. Chem. Soc. Perkin Trans II , pp. 1160
    • Bhatt, M.V.1    Ravindranathan, M.2
  • 36
    • 84982473548 scopus 로고
    • Acyliminium 3. Reaction of acyliminium salts with Grignard-reagents
    • Bartfeld, H.D.; Flitsch, W.; Gurke, K. Acyliminium 3. Reaction of acyliminium salts with Grignard-reagents. Chem. Ber. 1974, 107, 189.
    • (1974) Chem. Ber. , vol.107 , pp. 189
    • Bartfeld, H.D.1    Flitsch, W.2    Gurke, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.