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ChemicalBook CAS DataBase List 2-[(4-METHYLPHENYL)METHYLENE]-1H-INDENE-1,3(2H)-DIONE
15875-51-1

2-[(4-METHYLPHENYL)METHYLENE]-1H-INDENE-1,3(2H)-DIONE synthesis

7synthesis methods
16089-63-7 Synthesis
METHYL[(4-METHYLPHENYL)METHYLENE]AMMONIUMOLATE

16089-63-7
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2-[(4-METHYLPHENYL)METHYLENE]-1H-INDENE-1,3(2H)-DIONE

15875-51-1
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Yield:15875-51-1 89%

Reaction Conditions:

in dichloromethane at 80; for 2 h;Sealed tube;

Steps:

4.2. Reactions of β-diketones (1,3-indandione (2), barbituric acid (3), and dimedone (4)) with acyclic nitrones -O+N(Me)C(H)Ar (1) (Ar=C6H5 (1a), 4-MeC6H4 (1b), 2,4,6-Me3C6H2 (1c), C6H4-C2H-C6H4 (1d)) in CH2Cl2

General procedure: A solution of 1,3-indandione 2 (60.0 mg, 0.410 mmol) or a suspension of barbituric acid 3 (60.0 mg, 0.468 mmol) or dimedone 4 (60.0 mg, 0.428 mmol) in CH2Cl2 (3.0 mL) was added at room temperature to the appropriate nitrone 1 (1.2 equiv) and the mixture was heated at 80 °C in a sealed stainless steel tube for 2 h (in the case of 2 and 4) or 12 h (in the case of 3) and the progress of the reaction was monitored by TLC. After evaporation of the solvent in vacuum to dryness, the crude residue was purified by column chromatography on silica (CH2Cl2 as the eluent) followed by evaporation of the solvent in vacuum to give the final products 2'a-2'd, 3'a-3'd, or 4'a-4'd and/or 4a-4b, respectively.The reaction of 4 with 1a or 1b, in methanol at 80 °C for 4 h, leads to the formation of the dimmers 4a or 4b, respectively, as the exclusive detected products with ca. 80% yield.

References:

Lasri, Jamal;Gajewski, Grzegorz;Guedes Da Silva, M. Fátima C.;Kuznetsov, Maxim L.;Fernandes, Ricardo R.;Pombeiro, Armando J.L. [Tetrahedron,2012,vol. 68,# 35,p. 7019 - 7027] Location in patent:experimental part

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