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Volumn , Issue 4, 2003, Pages 771-783

Synthesis of pyrrole derivatives through functionalization of 3,4-bis(lithiomethyl)dihydropyrroles

Author keywords

Carbanions; Cyclization; Lithiation; Nitrogen heterocycles

Indexed keywords

1 (4 METHYLPHENYL) 3 [PHENYL(TRIMETHYLSILYL)METHYL] 4 (TRIMETHYLSILYLMETHYL) 1H PYRROLE; 1 (4 METHYLPHENYL) 3,4 BIS[PHENYL(TRIMETHYLSILYL)METHYL] 1H PYRROLE; 1,2,3,4,5,6 HEXAHYDRO 5 (4 METHYLPHENYL)PYRROLO[3,4 C]PYRROLE; 2 (4 METHYLPHENYL) 5 PHENYL 2,4,5,6 TETRAHYDROCYCLOPENTA[C]PYRROL 5 OL; 2 (4 METHYLPHENYL) 5 PROPYL 2,4,5,6 TETRAHYDROCYCLOPENTA[C]PYRROL 5 OL; 2 BENZYL 1,2,3,4,5,6 HEXAHYDRO 5 (4 METHYLPHENYL)PYRROLO[3,4 C]PYRROLE; 2 BUTYL 1,2,3,4,5,6 HEXAHYDRO 5 (4 METHYLPHENYL)PYRROLO[3,4 C]PYRROLE; 2,3,4,11 TETRAHYDRO 2 (4 METHYLPHENYL) 1H [1,6]BENZODIOXOCINO[3,4 C]PYRROLE; 2,4,5,6 TETRAHYDRO 2 (4 METHYLPHENYL) 4,5,5 TRIPHENYLSILOLO[3,4 C] PYRROLE; 2,4,5,6 TETRAHYDRO 5,5 DIMETHYL 2 (4 METHYLPHENYL) 4,6 DIPHENYLSILOLO[3,4 C]PYRROLE; 3 (1 DEUTERIOETHYL) 4 (DEUTERIOMETHYL) 1 (4 METHYLPHENYL) 1H PYRROLE; 3 (2 CYCLOPROPYL 2 OXOETHYL) 4 METHYL 1 (4 METHYLPHENYL) 1H PYRROLE; 3 (2 HYDROXY 1,2 DIMETHYLPROPYL) 4 (2 HYDROXY 2 METHYLPROPYL) 1 (4 METHYLPHENYL) 1H PYRROLE; 3 (DEUTERIOMETHYL) 4 [(DEUTERIOPHENYL)METHYL] 1 (4 METHYLPHENYL) 1H PYRROLE; 3 DEUTERIOMETHYL 4 (3 METHYL 2 OXOBUTYL) 1 (4 METHYLPHENYL) 1H PYRROLE; 3 METHYL 1 (4 METHYLPHENYL) 4 (2 OXO 2 PHENYLETHYL) 1H PYRROLE; 3 METHYL 1 (4 METHYLPHENYL) 4 (2 OXOBUTYL) 1H PYRROLE; 3 METHYL 1 (4 METHYLPHENYL) 4 (2 OXOPENTYL) 1H PYRROLE; 3 METHYL 1 (4 METHYLPHENYL) 4 (2 OXOPROPYL) 1H PYRROLE; 3 METHYL 4 (3 METHYL 2 OXOBUTYL) 1 (4 METHYLPHENYL) 1H PYRROLE; 3,4 BIS(DEUTERIOPHENYLMETHYL) 1 (4 METHYLPHENYL) 1H PYRROLE; 3,4 BIS(LITHIOMETHYL)DIHYDROPYRROLE; 5 CYCLOPROPYL 2 (4 METHYLPHENYL) 2,4,5,6 TETRAHYDROCYCLOPENTA[C] PYRROL 5 OL; 5 ETHYL 2 (4 METHYLPHENYL) 2,4,5,6 TETRAHYDROCYCLOPENTA[C]PYRROL 5 OL; 5 ISOPROPYL 2 (4 METHYLPHENYL) 2,4,5,6 TETRAHYDROCYCLOPENTA[C]PYRROL 5 OL; 5 METHYL 2 (4 METHYLPHENYL) 2,4,5,6 TETRAHYDROCYCLOPENTA[C]PYRROL 5 OL; LITHIUM DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037329872     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390120     Document Type: Article
Times cited : (24)

References (26)
  • 3
    • 33845278764 scopus 로고
    • For the synthesis of tetrahydrofurans see for instance: C. A. Broka, W. J. Lee, T. Shen, J. Org. Chem. 1988, 53, 1336-1338.
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    • Broka, C.A.1    Lee, W.J.2    Shen, T.3
  • 21
    • 0028260787 scopus 로고
    • It is known that a major limitation of the carbolithiation reactions is that 1,2-disubstituted olefinic systems do not undergo these reactions: W. F. Bailey, K. V. Gavaskar, Tetrahedron 1994, 50, 5957-5970.
    • (1994) Tetrahedron , vol.50 , pp. 5957-5970
    • Bailey, W.F.1    Gavaskar, K.V.2
  • 22
    • 0001386975 scopus 로고
    • The ambiguous role of this diamine (especially in THF) is underlined in: D. B. Collum, Acc. Chem. Res. 1992, 25, 448-454.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 448-454
    • Collum, D.B.1
  • 24
    • 0013351009 scopus 로고    scopus 로고
    • note
    • Treatment with tributyltin chloride or diphenyl disulfide did not yield functionalized derivatives of 11 and, moreover, further warming to room temperature afforded ketone 7e instead of the expected alcohol 8e.
  • 25
    • 19044383556 scopus 로고    scopus 로고
    • We have also recently reported the different behavior of o-lithioaryl ethers in THF or in diethyl ether: J. Barluenga, F. J. Fañanás, R. Sanz, C. Marcos, Org. Lett. 2002, 4, 1587-1590 and 2225-2228.
    • (2002) Org. Lett. , vol.4 , pp. 1587-1590
    • Barluenga, J.1    Fañanás, F.J.2    Sanz, R.3    Marcos, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.