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Volumn 2, Issue 1, 2005, Pages 29-32

Synthesis and transformations of ne spiro-4-piperidines. Acetyl migration in 1-acetyl-1′-benzyl-4-methyl-3, 4-dihydrospiro [(1H)quinoline-2,4′-piperidines] under debenzylation conditions

Author keywords

Acetyl migration; Debenzylation; Friedel Craft alkylation; Intramolecular alkene; Spiropiperidines

Indexed keywords


EID: 33748980390     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178053400234     Document Type: Review
Times cited : (10)

References (37)
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    • Pharmaceutical Substances, Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D.; Eds.; Thieme: Stuttgart, 1999.
  • 3
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    • Kouznetsov, V.V. Chem. Abst., 1991, 115, 158.846h.
    • (a) Kouznetsov, V.V. Chem. Abst., 1991, 115, 158.846h.
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    • 46149118776 scopus 로고    scopus 로고
    • Kouznetsov, V. Chem. Abstr., 1998, 128, 48.123f.
    • Kouznetsov, V. Chem. Abstr., 1998, 128, 48.123f.
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    • 46149120940 scopus 로고    scopus 로고
    • Kuznetsov, V.V.; Gaivoronskaya, L.A.; Fomichov, A.A.; Romero, R.M.; Prostakov, N.S. Chem. Abst., 1988, 108, 150.252w.
    • (a) Kuznetsov, V.V.; Gaivoronskaya, L.A.; Fomichov, A.A.; Romero, R.M.; Prostakov, N.S. Chem. Abst., 1988, 108, 150.252w.
  • 28
    • 46149108252 scopus 로고    scopus 로고
    • Kuznetsov, V.V.; Gaivoronskaya, L.A.; Fomichov, A.A.; Romero, R.M.; Prostakov, N.S. Chem. Abst., 1988, 108, 131.537b.
    • (a) Kuznetsov, V.V.; Gaivoronskaya, L.A.; Fomichov, A.A.; Romero, R.M.; Prostakov, N.S. Chem. Abst., 1988, 108, 131.537b.
  • 33
    • 46149127475 scopus 로고    scopus 로고
    • Basic character of nitrogen atoms in 3,4-dihydro-4-methylspiro[(1H)quinoline-2,4′-piperidine] was calculated in terms of the atomic charges on nitrogen atoms using the Partial Equalization of Orbital Electronegativity (PEOE) method. Piperidine nitrogen atom has major atomic charge (-0.3174).
    • Basic character of nitrogen atoms in 3,4-dihydro-4-methylspiro[(1H)quinoline-2,4′-piperidine] was calculated in terms of the atomic charges on nitrogen atoms using the Partial Equalization of Orbital Electronegativity (PEOE) method. Piperidine nitrogen atom has major atomic charge (-0.3174).
  • 35
    • 46149086947 scopus 로고    scopus 로고
    • Selective spectral data for compounds (3-5, Data for compound 3c: This compound was isolated (88, as yellow viscous liquid; IR (KBr) vC=0 3410 cm-1.13C NMR (100 MHz, CDCl3, δ 20.4, 20.6, 26.7, 34.9, 39.0, 48.8 (spiro, 49.4, 49.5, 49.8, 63.4, 114.5, 116.9, 125.8, 126.1, 127.0, 127.4, 127.5, 128.0, 129.2, 129.1(, 138.4, 140.6; GC-MS: tR 34.71 min, Mass spectrum (El, m/z, 320 (M, 5, 279, M-C3H7, 33, 214, M-C7H8N, 6, 185, M-C9Hl'3N, 2, 172, M-C10H14N, 62, 158, M-C11H1'6N, 2, 91 PhCH2, 100, Calcd for C22H28N2: C, 82.45; H, 8.81; N, 8.74, Found: C, 82.51; H, 8.96; N, 8.75
    • 2: C, 82.45; H, 8.81; N, 8.74%. Found: C, 82.51; H, 8.96; N, 8.75%.
  • 36
    • 46149089320 scopus 로고    scopus 로고
    • Data for compound 4c: This compound was isolated (86, as yellow very viscous liquid; IR (KBr) vC=0 1666 cm-1.13C NMR (100 MHz, CDCl3, δ 21.2, 26.68, ) 29.2, 29.7, 31.8, 36.7, 44.7, 50.3, ) 50.8, 61.2 (spiro, 62.7, 126.4, 126.5, 126.9, 128.0, 128.1, 128.2, 129.0, 129.1, 135.6, 137.8, 138.6, 140.1, 172.2; GC-MS: tR 44.39 min, Mass spectrum (EI, m/z, ) 362 (M+≥, 7, 319, M-C2H3O, 26),271, M-C7H7, 7, 230, M-C9H:10N, 9, 186 [M-C11H14NO, 31, 146, M-C14H18NO, 53, 91, M-C17H23N2O, 100, Anal. Calcd for C24H30N2O: C, 79.52; H, 8.34; N, 7.73, Found: C, 79.33; H, 8.56; N, 7.58, Data for compound 5c: This compound was is
    • 2O: C, 74.96; H, 8.88; N, 10.28%. Found: C, 74.71; H, 9.06; N, 10.05%.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.