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Volumn , Issue 10, 2008, Pages 1479-1482

Synthesis of new cyclopropanated tryptamine analogues

Author keywords

Cyclopropanes; Indoles; Titanium; Transition metals; Tryptamines

Indexed keywords

ACETONITRILE DERIVATIVE; AMINE; CYCLOPROPANE DERIVATIVE; INDOLE DERIVATIVE; TRYPTAMINE DERIVATIVE;

EID: 46449100062     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078426     Document Type: Article
Times cited : (5)

References (40)
  • 2
    • 46449139176 scopus 로고    scopus 로고
    • Houben-Weyl, E17a-c; de Meijere, A., Ed.; Thieme: Stuttgart, 1997.
    • (b) Houben-Weyl, Vol. E17a-c; de Meijere, A., Ed.; Thieme: Stuttgart, 1997.
  • 12
    • 0016607018 scopus 로고    scopus 로고
    • N-Cyclopropyltryptamine was also described as a potent monoamine oxidase inhibitor. See: Winn, M.; Horrom, B. W.; Rasmussen, R. R.; Chappell, E. B.; Plotnikoff, N. P. J. Med. Chem. 1975, 18, 437.
    • (b) N-Cyclopropyltryptamine was also described as a potent monoamine oxidase inhibitor. See: Winn, M.; Horrom, B. W.; Rasmussen, R. R.; Chappell, E. B.; Plotnikoff, N. P. J. Med. Chem. 1975, 18, 437.
  • 22
    • 33748630852 scopus 로고    scopus 로고
    • An alternative approach involving the titanium-mediated cyclopropanation of N,N-dialkylamides should be envisioned, but requires the preparation of the amides. For the reaction, see: (a) Chaplinski, V, de Meijere, A. Angew. Chem, Int. Ed. Engl. 1996, 35, 413
    • An alternative approach involving the titanium-mediated cyclopropanation of N,N-dialkylamides should be envisioned, but requires the preparation of the amides. For the reaction, see: (a) Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413.
  • 24
    • 0001581110 scopus 로고    scopus 로고
    • For related applications, see: c
    • For related applications, see: (c) Cao, B.; Xiao, D.; Joullié, M. M. Org. Lett. 1999, 1, 1799.
    • (1999) Org. Lett , vol.1 , pp. 1799
    • Cao, B.1    Xiao, D.2    Joullié, M.M.3
  • 33
    • 46449120890 scopus 로고    scopus 로고
    • The ketone by-product might also be obtained by the hydrolysis of metallacycle B (Scheme 2). This assumption was ruled out by deuterolysis of the reaction media (no trace of deuterium was observed on the methyl moiety).
    • The ketone by-product might also be obtained by the hydrolysis of metallacycle B (Scheme 2). This assumption was ruled out by deuterolysis of the reaction media (no trace of deuterium was observed on the methyl moiety).
  • 36
    • 46449104796 scopus 로고    scopus 로고
    • General Procedure for the MeTi(Oi-Pr) 3-Mediated Cyclopropanation of Nitriles 10a-c and 11a,b (Table 1, To a solution of the nitrile (1 mmol) and MeTi(Oi-Pr)3 (1.5 mmol) in THF (10 mL) was added dropwise under argon the Grignard reagent (1.5 mmol, The yellow solution darkened gradually within 5 min. After stirring for 1.5 h, BF3-OEt2 was added (2 mmol, After 30 min, the dark mixture was quenched with 1 M HC1 (10 mL, EtOAc (20 mL) was added, followed by 3 M NaOH (10 mL, The mixture was stirred until the blue aqueous solution become white. The aqueous phase was extracted with EtOAc (2 x 20 mL, After drying (MgSO4) and evaporation of the solvents, the crude material was purified by flash chromatography EtOAc
    • 4) and evaporation of the solvents, the crude material was purified by flash chromatography (EtOAc).
  • 37
    • 46449128107 scopus 로고    scopus 로고
    • 2S 327.1167; found: 327.1169.
    • 2S 327.1167; found: 327.1169.
  • 38
    • 46449089009 scopus 로고    scopus 로고
    • The cyclopropanation of unprotected 8 gave only a low yield of the primary cyclopropylamine.
    • The cyclopropanation of unprotected 8 gave only a low yield of the primary cyclopropylamine.
  • 40
    • 46449102278 scopus 로고    scopus 로고
    • Selected data: N,N-Dimethyl-1, 1-benzenesulfonyl-lH-indol-3-yl)methyl]cyclopropylamine (6a, yellow oil. IR (neat, 3365, 2916, 2845, 1634, 1445, 1264, 1119 cm-1. 1H NMR (300 MHz, CDCl3, δ, 0.25-0.57 (m, 4 H, 2.45 (s, 6 H, 3.01 (s, 2 H, 7.25-7.52 (m, 7 H, 7.80-7.83 (m, 2 H, 7.98 (d, J, 8.1 Hz, 1 H, 13C NMR (75 MHz, CDCl3, δ, 13.3,21.1,40.9,43.7, 113.9, 119.6, 120.3, 123.3, 124.2, 124.7,126.5,129.1,131.7, 133.7,135.1,138.0. HRMS (El, mlz [M, calcd for C 20H22N2O2S: 354.1402; found: 354.1398. N,N-Dimethyl-1, 1-methyl-2-vinyl-1H- indol-3-yl)methyl]cyclopropylamine (7a, yellow oil. IR (neat, 3054, 2986, 2845, 1628, 1437, 1262 cm-1. 1HNMR (300 MHz, CDCl 3, δ, 0.30-0.55 (m, 4 H, 2.63 (s, 6 H, 3.30 (s, 2 H, 3.70 (s, 3 H, 5.50 dd, J
    • 2: 255.1861; found: 255.1855.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.