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Synthesis 2008(20): 3289-3294  
DOI: 10.1055/s-0028-1083157
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Novel, One-Pot, Efficient Synthesis of 2-Aroyl-1,4-diaryl-7,9-dimethyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-triones

Mehdi Adib*a, Mohammad Hosein Sayahia, Hakimeh Ziyadia, Long-Guan Zhub, Hamid Reza Bijanzadehc
a School of Chemistry, University College of Science, University of Tehran, P.O. Box 14155-6455, Tehran, Iran
Fax: +98(21)66495291; e-Mail: madib@khayam.ut.ac.ir;
b Chemistry Department, Zhejiang University, Hangzhou 310027, P. R. of China
c Department of Chemistry, Tarbiat Modarres University, P.O. Box 14115-175, Tehran, Iran
Further Information

Publication History

Received 8 February 2008
Publication Date:
25 September 2008 (online)

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Abstract

A novel and efficient synthesis of 2-aroyl-1,4-diaryl-7,9-dimethyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-triones is described. The reactive 1:1 zwitterionic intermediate, formed by the addition of triphenylphosphine to diaroylacetylenes, was trapped by a Knoevenagel condensation product prepared in situ by reaction of N,N-dimethylbarbituric acid and aromatic aldehydes, to afford the title compounds in excellent yields under mild reaction conditions.

Key words

spiro compounds - cyclopentadienes - cyclizations - aldehydes­ - alkynes - heterocycles

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X-ray crystallographic data for compound 6b: Empirical formula: C30H24N2O4; Crystal system = orthorhombic; Space group P212121; Unit cell dimensions: a = 9.4114 (13) Å, b = 14.890 (2) Å, c = 18.003 (3) Å; V = 2522.79 (6) ų; T = 295 (2) K; Z = 4; D calcd = 1.255 g˙cm-³; µ (Mo-Kα) = 0.084 mm-¹; 13788 reflections measured, 2689 unique reflections (R int = 0.057), 1671 observed reflections, final R1 = 0.050, wR2 = 0.119 for I > 2σ(I). CCDC 656637 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.