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Volumn 41, Issue 12, 2000, Pages 1883-1887

Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ-lactams via a UDC strategy

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTAM DERIVATIVE; ISONITRILE DERIVATIVE; PIPERAZINE DERIVATIVE;

EID: 0034681853     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00052-6     Document Type: Article
Times cited : (71)

References (30)
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    • (a) Eds.; Elsevier Science: Oxford
    • (a) Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries; Tetrahedron Organic Chemistry Series, Volume 17; Obrecht, D.; Villalgordo, J. M., Eds.; Elsevier Science: Oxford, 1998.
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    • Obrecht, D.1    Villalgordo, J.M.2
  • 17
    • 0030443529 scopus 로고    scopus 로고
    • (a) Hulme, C.; Tang, S.-Y.; Burns, C. J.; Morize, I.; Labaudiniere, R. J. Org. Chem. 1998, 63, 8021. Keating, T. A.; Armstrong, R. W. J. Org. Chem. 1996, 61, 8935.
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    • Keating, T.A.1    Armstrong, R.W.2
  • 18
    • 0032191453 scopus 로고    scopus 로고
    • Note: The preparation of the safety-catch linker resin is reported by Elemental analysis indicated a loading of 0.8 mmol/g
    • Note: The preparation of the safety-catch linker resin is reported by: Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227. Elemental analysis indicated a loading of 0.8 mmol/g.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7227
    • Hulme, C.1    Peng, J.2    Morton, G.3    Salvino, J.M.4    Herpin, T.5    Labaudiniere, R.6
  • 19
    • 27844466269 scopus 로고
    • 4. Please note that the stability of this aldehyde is limited and the use of freshly prepared batches is advised. See
    • 4. Please note that the stability of this aldehyde is limited and the use of freshly prepared batches is advised. See: Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3815
    • Nahm, S.1    Weinreb, S.M.2
  • 21
    • 84992237321 scopus 로고    scopus 로고
    • Note: Methyl ester formation is postulated to proceed via an intermediate N-acyliminium ion
    • Note: Methyl ester formation is postulated to proceed via an intermediate N-acyliminium ion.
  • 22
    • 84992237323 scopus 로고    scopus 로고
    • Purchased from Argonaut® technologies
    • Purchased from Argonaut® technologies.
  • 23
    • 84992235319 scopus 로고    scopus 로고
    • 3CN to 100% over 5 min. HPLC was interfaced with APCI techniques
    • 3CN to 100% over 5 min. HPLC was interfaced with APCI techniques.
  • 24
    • 0343902739 scopus 로고    scopus 로고
    • Org Poster 232
    • The preparation of this resin was recently reported by workers at Amgen It is prepared in five steps from 4-(4-hydroxyphenyl)-cyclohexanone using Merrifield as the base resin. Loading in the 0.7-0.8 mmol/g range was achieved and reactions can be monitered by on-bead FTIR
    • The preparation of this resin was recently reported by workers at Amgen: Piscopio, A. Org Poster 232, Las Vegas Am. Chem. Soc. Meeting, 1997. It is prepared in five steps from 4-(4-hydroxyphenyl)-cyclohexanone using Merrifield as the base resin. Loading in the 0.7-0.8 mmol/g range was achieved and reactions can be monitered by on-bead FTIR.
    • (1997) Las Vegas Am. Chem. Soc. Meeting
    • Piscopio, A.1
  • 27
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    • (a) Note also that β-lactam formation was not investigated. Reaction of N-BOC-α-amino aldehydes in the Ugi MCR+acid treatment will predominantly produce imidazolines as reported in
    • (a) Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935. Note also that β-lactam formation was not investigated. Reaction of N-BOC-α-amino aldehydes in the Ugi MCR+acid treatment will predominantly produce imidazolines as reported in
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 935
    • Baldwin, J.E.1    Hulme, C.2    Schofield, C.J.3    Edwards, A.J.4
  • 30
    • 0032191453 scopus 로고    scopus 로고
    • Note: Mono-N-BOC diamines are available in three steps as reported by Krapcho
    • Hulme, C.; Peng, J.; Louridas, B.; Menard, P.; Krolikowski, P.; Kumar, N. V. Tetrahedron Lett. 1998, 39, 7227. Note: Mono-N-BOC diamines are available in three steps as reported by Krapcho, A. P.; Maresh, M. J.; Lunn, J. Synth. Comm. 1993, 23, 2443.
    • (1993) Synth. Comm. , vol.23 , pp. 2443
    • Maresh, A.P.1    Lunn, M.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.