A general and practical preparation of alkylidene Meldrum's acids

Tetrahedron Letters

Volumn 48, Issue 40, 2007, Pages 7072-7074

  Dumas, Aaron M ^a   Seed, Adam ^a   Zorzitto, Alexander K ^a   Fillion, Eric ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKENE DERIVATIVE; BENZENE; MELDRUM ACID; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; KNOEVENAGEL CONDENSATION; REACTION ANALYSIS; SCALE UP; SYNTHESIS;

EID: 34548390568     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.012     Document Type: Article

References (25)

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3. Fillion E., Dumas A.M., and Hogg S.A. J. Org. Chem. 71 (2006) 9899-9902 and references cited therein
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21. Reported as solvent for the preparation of 2- and 3-indolydene Meldrum's acids:. Benzies D.W.M., Fresneda P.M., Jones R.A., and McNab H. J. Chem. Soc., Perkin Trans. 1 (1986) 1651-1654
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23. 1H NMR analysis of the crude reaction mixture. The following characteristic peaks were integrated to determine the ratios: benzaldehyde, δ ∼ 10.0 (s, 1H); 3a, δ ∼ 8.6 (s, 1H); 4a, δ ∼ 4.68-4.61 (m, 3H).
24. 4, and concentrating dry or by removal of benzene by rotary evaporation and recrystallizing the resulting solid from MeOH.
25. For example, as reported by Bigi (Ref. 5a), the condensation of 4-chlorobenzaldehyde with Meldrum's acid in water gave an 86:14 mixture of 3:4, from which the AMA was isolated in 60% yield.