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Volumn , Issue 9, 2008, Pages 1402-1406

A novel method for the high-pressure-promoted, uncatalyzed aza-Michael reaction of nitrogen heterocycles with enones in water

Author keywords

Aza michael reaction; Enones; High pressure reaction; Nitrogen heterocycles; Water

Indexed keywords

HETEROCYCLIC COMPOUND; NITROGEN; SOLVENT; WATER;

EID: 45749122391     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072594     Document Type: Article
Times cited : (36)

References (103)
  • 1
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    • High-Pressure Organic Chemistry, Part 33. For Part 32, see: Kumamoto, K.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2006, 1968.
    • High-Pressure Organic Chemistry, Part 33. For Part 32, see: Kumamoto, K.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2006, 1968.
  • 85
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    • There is some controversy regarding organic reactions in or on water, see: a
    • There is some controversy regarding organic reactions in or on water, see: (a) Brogan, A. P.; Dickerson, T. J.; Janda, K. D. Angew. Chem. Int. Ed. 2006, 45, 8100.
    • (2006) Angew. Chem. Int. Ed , vol.45 , pp. 8100
    • Brogan, A.P.1    Dickerson, T.J.2    Janda, K.D.3
  • 89
    • 0000574863 scopus 로고    scopus 로고
    • For the example of high-pressure-promoted aza-Michael reactions in water, see: a
    • For the example of high-pressure-promoted aza-Michael reactions in water, see: (a) Jenner, G. J Phys. Org. Chem. 1999, 12, 619.
    • (1999) J Phys. Org. Chem , vol.12 , pp. 619
    • Jenner, G.1
  • 90
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    • See also: b
    • See also: (b) Ref. 15b.
    • , vol.15 b
    • Ref1
  • 92
    • 45749101600 scopus 로고    scopus 로고
    • 2-i-PrOH) to afford the pure adduct 3.
    • 2-i-PrOH) to afford the pure adduct 3.
  • 93
    • 24744451593 scopus 로고    scopus 로고
    • a = 14.75 in DMSO) in the absence of any dehydrating agents is quite unique, and we are currently performing experiments to explore the general scope of this reaction. See also: Kumamoto, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2005, 2254.
    • a = 14.75 in DMSO) in the absence of any dehydrating agents is quite unique, and we are currently performing experiments to explore the general scope of this reaction. See also: Kumamoto, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2005, 2254.
  • 94
    • 45749153287 scopus 로고    scopus 로고
    • All new compounds gave satisfactory analytical and spectral data
    • All new compounds gave satisfactory analytical and spectral data.
  • 95
    • 45749141564 scopus 로고    scopus 로고
    • The higher reactivity of purine (1g) at the N9 position is well established. For example, see ref. 6. Compound 3q: mp 123-125°C (hexane-CH2Cl2, FT-IR (KBr, ν, 1698, 1595, 1576, 1496, 1413 cm-1. 1H NMR (400 MHz, CDCl3, δ, 1.85 (1 H, dddd, J, 14.0, 12.0, 5.4, 3.6 Hz, 2.16-2.23 (1 H, m, 2.32-2.39 (1 H, m, 2.48-2.62 (3 H, m, 2.95 (1 H, ddt, J, 14.1, 4.9, 1.7 Hz, 3.26 (1 H, dd, J, 14.1, 11.7 Hz, 4.89 (1 H, tt, J, 11.5, 4.2 Hz, 8.13 (1 H, s, 8.98 (1 H, s, 9.17 (1 H, s, 13C NMR (100 MHz, CDCl3, δ, 22.0, 30.7, 40.5, 46.9, 54.4, 134.6, 143.2, 149.1, 150.9, 152.4, 206.3. Compound 3r: mp 143-144°C (hexane-CH2Cl2, FT-IR (KBr, ν, 1708, 1606, 1559, 1488, 1412 cm-1. 1H NMR (400 MHz, CDCl3, δ, 1.83-1.96 (1 H, m, 2.17-2.26 (1 H, m, 2.37 1 H, ddt, J, 14.6, 1
    • 3): δ = 21.9, 31.3, 40.4, 47.6, 55.7, 124.4, 140.0, 145.5, 153.7, 161.0, 205.3.
  • 96
    • 45749156305 scopus 로고    scopus 로고
    • Compound 3d: mp 69-70°C (hexane-CH2Cl2, FT-IR (KBr, ν, 1685, 1596, 1521, 1448 cm-1. 1H NMR (400 MHz, CDCl3, δ, 3.60 (2 H, t, J, 6.4 Hz, 4.65 (2 H, t, J, 6.4 Hz, 7.47 (2 H, m, 7.59 (1 H, tt, J, 7.3, 1.2 Hz, 7.91-7.95 (3 H, m, 8.23 (1 H, s, 13C NMR (100 MHz, CDCl 3, δ, 37.9, 44.0, 128.0 (2x, 128.7 (2x, 133.7, 136.0, 144.0, 152.0, 196.5. Compound 3e: mp 87-89°C (hexane-CH 2Cl2, FT-IR (KBr, ν, 1687, 1538 cm-1. 1H NMR (400 MHz, CDCl3, δ, 3.50 (2 H, t, J, 6.1 Hz, 4.55 (2 H, t, J, 6.1 Hz, 7.50 (2 H, t, J, 7.8 Hz, 7.62 (1 H, m, 7.93 (2 H, m, 8.34 (2 H, s, 13C NMR (100 MHz, CDCl3, δ, 39.2, 39.7, 128.0 (2x, 128.9 (2x, 134.2, 135.6, 143.2 2x, 195.8
    • 3): δ = 39.2, 39.7, 128.0 (2x), 128.9 (2x), 134.2, 135.6, 143.2 (2x), 195.8.
  • 97
    • 0037037978 scopus 로고    scopus 로고
    • For recent examples of imidazole-catalyzed Morita-Baylis-Hillman reactions, see: a
    • For recent examples of imidazole-catalyzed Morita-Baylis-Hillman reactions, see: (a) Luo, S.; Zhang, B.; He, J.; Janczuk, A.; Wang, P. G.; Cheng, J.-P. Tetrahedron Lett. 2002, 43, 7369.
    • (2002) Tetrahedron Lett , vol.43 , pp. 7369
    • Luo, S.1    Zhang, B.2    He, J.3    Janczuk, A.4    Wang, P.G.5    Cheng, J.-P.6
  • 103
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    • 2O, 0.6 GPa, 60°C, 20 h), except for methyl acrylate (87% conversion yield).
    • 2O, 0.6 GPa, 60°C, 20 h), except for methyl acrylate (87% conversion yield).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.