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Volumn 74, Issue 14, 2009, Pages 5090-5092

Direct synthesis of polyfunctionalized unsaturated δ-lactones and δ-lactams from α-alkenoyl α-carboxyl/carbamoyl ketene S,S-acetals under Vilsmeier conditions

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; DIRECT SYNTHESIS; EFFICIENT METHOD; VILSMEIER; VILSMEIER REAGENT;

EID: 67650376993     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900663z     Document Type: Article
Times cited : (14)

References (52)
  • 5
    • 0037154874 scopus 로고    scopus 로고
    • For selective examples on the synthesis of δ-lactones, see: a
    • For selective examples on the synthesis of δ-lactones, see: (a) Pàmies, O.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1261.
    • (2002) J. Org. Chem , vol.67 , pp. 1261
    • Pàmies, O.1    Bäckvall, J.-E.2
  • 14
    • 32144461175 scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Dieter, R. K. Tetrahedron 1986, 42, 3029.
    • (1986) Tetrahedron , vol.42 , pp. 3029
    • Dieter, R.K.1
  • 24
    • 16844377947 scopus 로고    scopus 로고
    • For [5 + 1] annulations, see: (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578.
    • For [5 + 1] annulations, see: (a) Bi, X.; Dong, D.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578.
  • 36
    • 56249085917 scopus 로고    scopus 로고
    • For a onepot synthesis of substituted pyridine-2,4(1H,3H)- diones from the reaction of acyl(carbamoyl)ketene S,S-acetals with N,N-dimethylformamide dimethyl acetal, see: (b) Li, Y.; Li, W.; Zhang, R.; Zhou, Y.; Dong, D. Synthesis 2008, 3411.
    • For a onepot synthesis of substituted pyridine-2,4(1H,3H)- diones from the reaction of acyl(carbamoyl)ketene S,S-acetals with N,N-dimethylformamide dimethyl acetal, see: (b) Li, Y.; Li, W.; Zhang, R.; Zhou, Y.; Dong, D. Synthesis 2008, 3411.
  • 37
    • 63849248236 scopus 로고    scopus 로고
    • For synthesis of dihydropyranones from the reaction of R-acetyl ketene S,Sacetals with aldehydes, see: (c) Ouyang, Y.; Huang, J.; Pan, W.; Liang, Y.; Yang, Y.; Dong, D. W. Eur. J. Org. Chem. 2009, 2003.
    • For synthesis of dihydropyranones from the reaction of R-acetyl ketene S,Sacetals with aldehydes, see: (c) Ouyang, Y.; Huang, J.; Pan, W.; Liang, Y.; Yang, Y.; Dong, D. W. Eur. J. Org. Chem. 2009, 2003.
  • 39
    • 67650492135 scopus 로고    scopus 로고
    • Vilsmeier reagents are commercially available and have found extensive applications in organic synthesis, see: (a) Meth-Cohn, O, Stanforth, S. P. In Comprehensive Organic Synthesis; Heathcock, C. H, Ed, Pergamon Press: New York, 1991; 2, p 777
    • Vilsmeier reagents are commercially available and have found extensive applications in organic synthesis, see: (a) Meth-Cohn, O.; Stanforth, S. P. In Comprehensive Organic Synthesis; Heathcock, C. H., Ed.; Pergamon Press: New York, 1991; Vol. 2, p 777.
  • 41
    • 0028822398 scopus 로고
    • For selected examples, see: c
    • For selected examples, see: (c) Meth-Cohn, O.; Taylor, D. L. Tetrahedron 1995, 51, 12869.
    • (1995) Tetrahedron , vol.51 , pp. 12869
    • Meth-Cohn, O.1    Taylor, D.L.2
  • 52
    • 67650485644 scopus 로고    scopus 로고
    • In our research, the corresponding 4-chloro-unsaturated δ-lactams were not obtained under the reaction conditions used
    • In our research, the corresponding 4-chloro-unsaturated δ-lactams were not obtained under the reaction conditions used.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.