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Volumn 66, Issue 31, 2010, Pages 5811-5818

A versatile PIFA-mediated approach to structurally diverse pyrrolo(benzo)diazepines from linear alkynylamides

Author keywords

Alkynylamides; Diazepines; Hypervalent iodine; PIFA; Reductive amination

Indexed keywords

DIAZEPINE DERIVATIVE; IODINE DERIVATIVE; PHENYLIODINE(III) BIS(TRIFLUOROACETATE); PYRROLO(BENZO) DIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77955466282     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.080     Document Type: Article
Times cited : (24)

References (48)
  • 9
    • 3843140700 scopus 로고    scopus 로고
    • K.K. Kothakonda, and D.S. Bose Bioorg. Med. Chem. Lett. 14 2004 4371 4373 For an application of this approach in the synthesis of tetrahydroisoquinolino- fused benzodiazepines, see:
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 4371-4373
    • Kothakonda, K.K.1    Bose, D.S.2
  • 16
    • 0003410653 scopus 로고
    • For some excellent books on the chemistry of hypervalent iodine reagents VCH New York, NY
    • For some excellent books on the chemistry of hypervalent iodine reagents, see: A. Varvoglis The Organic Chemistry of Polycoordinated Iodine 1992 VCH New York, NY
    • (1992) The Organic Chemistry of Polycoordinated Iodine
    • Varvoglis, A.1
  • 26
    • 77955473262 scopus 로고    scopus 로고
    • Note
    • N-Methoxyamides and N-phthalimidoamides are also known to generate stable acyl-nitrenium intermediates.
  • 34
    • 77955473021 scopus 로고    scopus 로고
    • Note
    • Although literature offers a great amount of examples related to the preparation of PBDs, the preparation of simple pyrrolodiazepines is much more limited. See, for example:
  • 40
    • 77955472526 scopus 로고    scopus 로고
    • Note
    • In previous non-published results from our group, we found that the presence of free amino, and also hydroxy groups are not compatible with the PIFA-assisted intramolecular heterocyclization of unsaturated amides.
  • 41
    • 68449100165 scopus 로고    scopus 로고
    • For some recent advances on the Sonogashira reaction
    • For some recent advances on the Sonogashira reaction, see: M.M. Heravi, and S. Sadjadi Tetrahedron 65 2009 7761 7775
    • (2009) Tetrahedron , vol.65 , pp. 7761-7775
    • Heravi, M.M.1    Sadjadi, S.2
  • 46
    • 77955467129 scopus 로고    scopus 로고
    • Note
    • The protection of 17 to afford 18 resulted to be a difficult task. Impossible, when benzyloxycarbonyl chloride was employed, and poorly satisfactory when benzyl para-nitrophenyl carbonate (BNC) was tested.
  • 47
    • 0028205009 scopus 로고
    • Several PBD derivatives similar to 21 with a piperazine substituent at C-11 position has also been targeted as pharmacophores: See, for example J.-Y. Mérour, F. Cossais, S. Piroëlle, and D. Mazéas J. Heterocycl. Chem. 31 1994 87 92 The natural product tilivalline presents the same core with a 3-indolyl substituent at C-11
    • (1994) J. Heterocycl. Chem. , vol.31 , pp. 87-92
    • Mérour, J.-Y.1    Cossais, F.2    Piroëlle, S.3    Mazéas, D.4
  • 48
    • 77955471886 scopus 로고    scopus 로고
    • Note
    • An excess of starting material was employed to avoid an undesired N,N′-diprotection process.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.