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Volumn 17, Issue 41, 2011, Pages 11559-11566

Controlled rearrangement of lactam-tethered allenols with brominating reagents: A combined experimental and theoretical study on α-versus β-keto lactam formation

Author keywords

allenes; chemoselectivity; lactams; reaction mechanisms; rearrangement

Indexed keywords

ALLENES; CHEMO-SELECTIVITY; LACTAMS; REACTION MECHANISM; REARRANGEMENT;

EID: 80053211492     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101160     Document Type: Article
Times cited : (31)

References (87)
  • 1
    • 80053190976 scopus 로고    scopus 로고
    • For reviews on allene chemistry, see
    • For reviews on allene chemistry, see
  • 8
    • 22944485617 scopus 로고    scopus 로고
    • S. Ma, Chem. Rev. 2005, 105, 2829
    • (2005) Chem. Rev. , vol.105 , pp. 2829
    • Ma, S.1
  • 10
    • 4544320494 scopus 로고    scopus 로고
    • (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim
    • Modern Allene Chemistry (Eds.:, N. Krause, A. S. K. Hashmi,), Wiley-VCH, Weinheim, 2004
    • (2004) Modern Allene Chemistry
  • 17
    • 80053184513 scopus 로고    scopus 로고
    • The tetramic acid unit is a structural feature found in many natural products and displays a wide spectrum of biological activities (representatives examples are antibacterial, antifungal, antitumor, antiviral, insecticide, and receptor antagonist activity)
    • The tetramic acid unit is a structural feature found in many natural products and displays a wide spectrum of biological activities (representatives examples are antibacterial, antifungal, antitumor, antiviral, insecticide, and receptor antagonist activity); for reviews, see
  • 20
    • 42149107087 scopus 로고    scopus 로고
    • for selected recent references, see
    • R. Schobert, A. Schlenk, Bioorg. Med. Chem. 2008, 16, 4203; for selected recent references, see
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 4203
    • Schobert, R.1    Schlenk, A.2
  • 29
    • 80053177688 scopus 로고    scopus 로고
    • Substituted quinolin-2-ones represent a class of important compounds that display a broad spectrum of biological and chemical functions; for selected references, see
    • Substituted quinolin-2-ones represent a class of important compounds that display a broad spectrum of biological and chemical functions; for selected references, see
  • 45
    • 80053215242 scopus 로고    scopus 로고
    • For a preliminary communication on part of this work, see
    • For a preliminary communication on part of this work, see
  • 46
    • 77949860743 scopus 로고    scopus 로고
    • for pioneering studies on electrophilic interaction of 2,3-allenols with electrophilic halogen reagents, see
    • B. Alcaide, P. Almendros, A. Luna, M. R. Torres, Adv. Synth. Catal. 2010, 352, 621; for pioneering studies on electrophilic interaction of 2,3-allenols with electrophilic halogen reagents, see
    • (2010) Adv. Synth. Catal. , vol.352 , pp. 621
    • Alcaide, B.1    Almendros, P.2    Luna, A.3    Torres, M.R.4
  • 57
    • 53849128160 scopus 로고    scopus 로고
    • Angew. Chem. 2007, 119, 6804
    • (2007) Angew. Chem. , vol.119 , pp. 6804
  • 60
    • 80053191459 scopus 로고    scopus 로고
    • See reference [5e]
    • See reference [5e]
  • 63
    • 80053181397 scopus 로고    scopus 로고
    • Diastereoselectivity is due to the exclusive or preferential formation of a diastereomer. Chemoselectivity arises from the exclusive cleavage of the C2-C3 bond of the β-lactam ring, whereas regioselectivity comes from sole attack to the proximal allene carbon atom with concomitant placement of the bromine to the central allene position
    • Diastereoselectivity is due to the exclusive or preferential formation of a diastereomer. Chemoselectivity arises from the exclusive cleavage of the C2-C3 bond of the β-lactam ring, whereas regioselectivity comes from sole attack to the proximal allene carbon atom with concomitant placement of the bromine to the central allene position.
  • 64
    • 80053177222 scopus 로고    scopus 로고
    • Attached ring adduct 3 i can be regarded as a hybrid of the pharmacologically relevant subunits of β-lactam and tetramic acid
    • Attached ring adduct 3 i can be regarded as a hybrid of the pharmacologically relevant subunits of β-lactam and tetramic acid.
  • 65
    • 80053215452 scopus 로고    scopus 로고
    • The mild basicity of molecular sieves should be responsible for this slight catalytic activity by deprotonation of the hydroxyl moiety to provide a nucleophilic alcoxide which facilitates the rearrangement
    • The mild basicity of molecular sieves should be responsible for this slight catalytic activity by deprotonation of the hydroxyl moiety to provide a nucleophilic alcoxide which facilitates the rearrangement.
  • 66
    • 80053200787 scopus 로고    scopus 로고
    • note
    • 2 (SHELXL-97). All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were included in calculated positions and refined riding on the respective carbon atoms. Final R(wR) values were R1=0.0433 and wR2=0.1082. CCDC-711362 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
  • 67
    • 80053193509 scopus 로고    scopus 로고
    • note
    • 2 (SHELXL-97). All non-hydrogen atoms were refined anisotropically. All hydrogen atoms were included in calculated positions and refined riding on the respective carbon atoms. Final R(wR) values were R1=0.0460 and wR2=0.1071. CCDC-765452 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
  • 69
    • 80053207432 scopus 로고    scopus 로고
    • 6 serotonin receptor antagonistic activities have been found in quinoline-2,4-diones with a quaternary carbon center at C-3. This β-keto lactam moiety is also the core of the natural product buchapine, exhibiting therapeutic activity; see, for example
    • 6 serotonin receptor antagonistic activities have been found in quinoline-2,4-diones with a quaternary carbon center at C-3. This β-keto lactam moiety is also the core of the natural product buchapine, exhibiting therapeutic activity; see, for example
  • 73
    • 80053213647 scopus 로고    scopus 로고
    • Experimental procedures as well as full spectroscopic and analytical data for compounds not included in the Experimental Section are described in the Supporting Information. It also contains copies of NMR spectra for all new compounds
    • Experimental procedures as well as full spectroscopic and analytical data for compounds not included in the Experimental Section are described in the Supporting Information. It also contains copies of NMR spectra for all new compounds.
  • 81
    • 0003418036 scopus 로고
    • (Ed.: D. R. Yarkony), World Scientific Publishing, Singapore
    • H. B. Schlegel, in Modern Electronic Structure Theory. (Ed.:, D. R. Yarkony,), World Scientific Publishing, Singapore, 1994.
    • (1994) Modern Electronic Structure Theory.
    • Schlegel, H.B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.