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Volumn 65, Issue 14, 2000, Pages 4326-4332

Synthesis and synthetic application of α-formylvinylphosphonates. Facile synthesis of phosphono-substituted heterocyclic compounds

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANION; HETEROCYCLIC COMPOUND; ISOCYANIC ACID DERIVATIVE; KETONE; PHOSPHONIC ACID DERIVATIVE;

EID: 0034647772     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000149t     Document Type: Article
Times cited : (34)

References (40)
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  • 3
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    • For a review of α-heteroatom-substituted vinyl anions, see: (a) Braun, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 430. For the preparation of α-hetero (B, Si, O, Se, Te)-substituted vinyl anions and their synthetic application, see, ref 9 and references therein.
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  • 7
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    • For the preparation of α-phosphonovinyl anion, via conjugate addition of nucleophiles to 1-alkynylphosphonates, see: (a) Gil, J. M.; Oh, D. Y. J. Org. Chem. 1999, 64, 2950. via transmetalation, see:
    • (1999) J. Org. Chem. , vol.64 , pp. 2950
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  • 10
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    • and references therein
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  • 11
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    • For isomerization of β-alkyl-α-phosphonio- or phosphonovinyl anion into the corresponding allyl anion, see, for examples: (a) Minami, T.; Shikita, S.; So, S.; Nakayama, M.; Yamamoto, I. J. Org. Chem. 1988, 53, 2937.
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  • 16
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    • For the synthesis of phosphono-substituted heterocyclic compounds, see, for examples: (a) Yuan, C.; Huang, W.; Onnis, V. Synthesis 1993, 473.
    • (1993) Synthesis , pp. 473
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    • note
    • Only 1,2-adduct products were produced even in the presence of the Cu(I) salt.
  • 24
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    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 2008
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    • 0000628893 scopus 로고    scopus 로고
    • and references therein
    • The stereochemistry was determined on the basis of the phosphorus-vinyl proton coupling constant, see: Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697 and references therein.
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  • 27
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    • For the synthesis of limited α-formylvinylphosphonates such as 1-formyl-1-propenylphosphonate and 2-amino-1-(formyl)vinylphosphonate, see (a) Al-Badri, H.; About-Jaudet, E.; Combret, J.-C.; Collignon, N. Synthesis 1995, 1401.
    • (1995) Synthesis , pp. 1401
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    • note
    • 1H NMR analysis (see Experimental Section).
  • 30
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    • note
    • 1H NMR, its isolation was not attempted.
  • 31
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    • note
    • Diethyl 1-formylpentylphosphonate, which is hydrogenation product of 5k, was isolated in 37% yield along with 7k. The structure was identified by comparison of spectral data with those of an authentic sample.
  • 32
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    • For intramolecular cycloadditions of 1,7-dienes with the carbonyl group on the C-1 carbon, see (a) Tietze, L, F.; Kiedrowski, G. v. Tetrahedron Lett. 1981, 22, 219.
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  • 34
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    • For hetero Diels-Alder reaction of α,β-unsaturated acylphosphonates with enol ethers, see, for example, Evans, D. A.; Johnson, J. S. J. Am. Chem. Soc. 1988, 110, 4895.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4895
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  • 38
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    • note
    • Although the compound 10 is composed of a single isomer, its stereochemical assignment was not made.
  • 40
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    • For the synthesis of pyrazole from the reaction of α-oxo ketene dithioacetals with hydrazine, see, a review: Dieter, R. K. Tetrahedron 1986, 42, 3029. See also ref 15b.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.