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Volumn 75, Issue 21, 2010, Pages 7408-7411

Synthesis of chlorinated bicyclic C-fused tetrahydrofuro[3,2- c ]azetidin-2-ones

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE ATOM; CLICK REACTION; DIASTEREOSELECTIVE; DICHLOROKETENE; IMIDATES; PHENYLACETYLENES; RADICAL CYCLIZATIONS; SIDE CHAINS; STAUDINGER REACTIONS; SYNTHETIC APPLICATION;

EID: 78049512273     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101045z     Document Type: Article
Times cited : (29)

References (77)
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    • It appears that additional activation of the β-lactam ring may not be absolutely essential for its biological activity, particularly with regard to the biological activities other than antibacteria.l; J. Med. Chem. 2005, 48, 6035
    • Hogan, P. C.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 15386 It appears that additional activation of the β-lactam ring may not be absolutely essential for its biological activity, particularly with regard to the biological activities other than antibacteria.l Kvrn, L.; Werder, M.; Hauser, H.; Carreira, E. M. J. Med. Chem. 2005, 48, 6035
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 15386
    • Hogan, P.C.1    Corey, E.J.2    Kvrn, L.3    Werder, M.4    Hauser, H.5    Carreira, E.M.6
  • 46
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    • A few reported molecules of this type have a nonactivated β-lactam ring and have been prepared by [2 + 2] cycloaddition of aryl or alkyl isocyantes to the parent 4,5-dihydrofuran
    • A few reported molecules of this type have a nonactivated β-lactam ring and have been prepared by [2 + 2] cycloaddition of aryl or alkyl isocyantes to the parent 4,5-dihydrofuran. Garcia-Martinez, C.; Taguchi, Y.; Oishi, A.; Hayamizu, K. Tetrahedron: Asymmetry 1998, 9, 955
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 955
    • Garcia-Martinez, C.1    Taguchi, Y.2    Oishi, A.3    Hayamizu, K.4
  • 50
    • 0347875871 scopus 로고    scopus 로고
    • The former suffers from low reactivity of the isocyanates and requires high pressure (800 MPa at 100 °C), and the latter forms unstable products in low yields accompanied by [4 + 2] cycloadducts. The trichloroacetyl group need be cleaved to obtain the stable products having no N-substituent. A cyclization by nucleophilic alkylation of the β-lactam enolate at subzero temperatures (-65 to -45 °C) has also been reported.; Synlett 1990, 684 For some refs of natural bioactive bicyclic hemiaminal ethers see, ref 11h and:; Org. Lett. 2009, 11, 3458
    • Abramski, W.; Urbanczyk-Lipkowska, Z.; Chmielewski, M. J. Carbohydr. Chem. 1997, 16, 63 The former suffers from low reactivity of the isocyanates and requires high pressure (800 MPa at 100 °C), and the latter forms unstable products in low yields accompanied by [4 + 2] cycloadducts. The trichloroacetyl group need be cleaved to obtain the stable products having no N-substituent. A cyclization by nucleophilic alkylation of the β-lactam enolate at subzero temperatures (-65 to -45 °C) has also been reported. Murakami, M.; Aoki, T.; Nagata, W. Synlett 1990, 684 For some refs of natural bioactive bicyclic hemiaminal ethers see, ref 11h and: Boal, B. W.; Schammel, A. W.; Garg, N. K. Org. Lett. 2009, 11, 3458
    • (1997) J. Carbohydr. Chem. , vol.16 , pp. 63
    • Abramski, W.1    Urbanczyk-Lipkowska, Z.2    Chmielewski, M.3    Murakami, M.4    Aoki, T.5    Nagata, W.6    Boal, B.W.7    Schammel, A.W.8    Garg, N.K.9
  • 57
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    • We could find only one example of application of CuCl/bpy-catalyzed ATRC for the synthesis of an N-fused bicyclic β-lactam in poor yield (28%)
    • We could find only one example of application of CuCl/bpy-catalyzed ATRC for the synthesis of an N-fused bicyclic β-lactam in poor yield (28%). Penfold, D. J.; Pike, K.; Genge, A.; Anson, M.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 10347
    • (2000) Tetrahedron Lett. , vol.41 , pp. 10347
    • Penfold, D.J.1    Pike, K.2    Genge, A.3    Anson, M.4    Kitteringham, J.5    Kilburn, J.D.6
  • 61
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    • See ref 11d and references cited therein for synthetic applications of β-alkylidenetetrahydrofurans and for such a natural bioactive compound
    • See ref 11d and references cited therein for synthetic applications of β-alkylidenetetrahydrofurans and for such a natural bioactive compound.
  • 64
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    • Triazolyl-β-lactams:; Antimicrob. Agents Chemother. 1979, 15, 209
    • Krivopalov, V. P.; Shkurko, O. P. Russ. Chem. Rev. 2005, 74, 339 Triazolyl-β-lactams: Neu, H.; Fu, K. Antimicrob. Agents Chemother. 1979, 15, 209
    • (2005) Russ. Chem. Rev. , vol.74 , pp. 339
    • Krivopalov, V.P.1    Shkurko, O.P.2    Neu, H.3    Fu, K.4
  • 74
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    • We could find only one report which described two examples of cycloaddition of ethyl formimidates with dichloroketene to form the corresponding 3,3-dichloro-β-lactams in negligible yields (7%).;, A few reports described cycloaddition of dichloroketene to some endocyclic imidates (5,6-dihydro-1,3-oxazines):; Acta Chem. Scand. 1996, 50, 922
    • We could find only one report which described two examples of cycloaddition of ethyl formimidates with dichloroketene to form the corresponding 3,3-dichloro-β-lactams in negligible yields (7%). Katagiri, N.; Niwa, R.; Kato, T. Chem. Pharm. Bull. 1983, 31, 2899 A few reports described cycloaddition of dichloroketene to some endocyclic imidates (5,6-dihydro-1,3-oxazines): Stajer, G.; Virag, M.; Szabo, A. E.; Bernath, G.; Sohar, P.; Sillanpaa, R. Acta Chem. Scand. 1996, 50, 922
    • (1983) Chem. Pharm. Bull. , vol.31 , pp. 2899
    • Katagiri, N.1    Niwa, R.2    Kato, T.3    Stajer, G.4    Virag, M.5    Szabo, A.E.6    Bernath, G.7    Sohar, P.8    Sillanpaa, R.9
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    • Exocyclic imidates (maleic isoimides) have also been described:; Helv. Chim. Acta 1983, 66, 362 These compounds form N-fused bicyclic and spirocyclic β-lactams, respectively
    • Sohar, P.; Stajer, G.; Pelczer, I.; Szabo, A. E.; Szunyog, J.; Bernath, G. Tetrahedron 1985, 41, 1721 Exocyclic imidates (maleic isoimides) have also been described: Capraro, H. G.; Winkler, T.; Martin, P. Helv. Chim. Acta 1983, 66, 362 These compounds form N-fused bicyclic and spirocyclic β-lactams, respectively.
    • (1985) Tetrahedron , vol.41 , pp. 1721
    • Sohar, P.1    Stajer, G.2    Pelczer, I.3    Szabo, A.E.4    Szunyog, J.5    Bernath, G.6    Capraro, H.G.7    Winkler, T.8    Martin, P.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.