Synthesis, Thermal and Photochemical Transformations of a few 4-Aryl-1,2-dipyridin-2-yl-but-2-ene-1,4-dione

Vidya Raman, Rakesh Natarajan


In an attempt to synthesize 5-aryl-3,3-dipyridin-2-yl-3H-furan-2-ones, several (Z)-4-aryl-1,2-(dipyridin-2-yl)but-2-ene-1,4-dione precursors were synthesized by the base- catalyzed reaction between 2,2’-pyridil and suitably substituted acetophenones. These novel dibenzoylalkene- type systems containing heteroatomatic rings underwent extensive decomposition under the influence of heat and E-Z isomerization under the influence of light.


Dibenzoylstyrenes, 2(3H)-furanones, 3(2H)-furanones,2,2’-pyridil, substituted acetophenones, condensation reaction.

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Gopidas KR, Lohray BB, Rajadurai S et al. Sensitized photorearrangement of 3,3,5-triaryl-2(3H)-furanones to 3,4,5-triaryl-2(5H)-furanones. Steady-state and laser flash photolysis investigations. J Org Chem 1987; 52: 2831-38.

Gopidas KR, Cyr DR, Das PK et al. Photochemical and thermal transformations of 3-benzyl-2(3H)-furanones and related substrates. J Org Chem 1987; 52: 5505-11.

Davis HF, Lohray BB, Gopidas KR et al. Photoinduced electron-transfer reactions of 2(3H)-furanones and bis(benzofuranones). Spectral and kinetic behavior of radicals and radical cations. J Org Chem 1985; 50: 3685-92.

Lohray BB, Kumar CV, Das PK et al. Photochemical and thermal transformations of 2(3H)-furanones and bis(benzofuranones). A laser flash photolysis study. J Am Chem Soc 1984; 106: 7352-59.

Kuhn LP, Lutz RE, Bauer CR. A Spectroscopic Study of cis- and trans-Dibenzoylethylenes and Related Compounds. J Am Chem Soc 1950; 72: 5058-63.

Yogev A, Mazur Y. Irradiation of Enol Lactones. J Am Chem Soc1965; 87: 3520-21.

Gutsche CD, Oude-Alink BAM. The photoinducedalcoholysis of 3,4-dihydrocoumarin and related compounds. J Am Chem Soc 1968; 90: 5855-61.

Krull IS, Arnold DR. The Hg senitized vapor phase photolysis of γ-crotonolactone and simple butenolides. Tetrahedron Lett 1969; 10: 1247-49.

Padwa A, Dehm D. Photochemical transformations of small ring carbonyl compounds. 68. Photochemical rearrangement in the 2(5H)-furanone system. J Am Chem Soc 1975; 97: 4779-81.

Padwa A, Brookhart T, Dehm D et al. Photochemical transformations of small ring carbonyl compounds. 101. Migratory aptitude studies in the photochemical rearrangement of 2(5H)-furanones. J Am Chem Soc 1978; 100: 8247-59.

Ohga K, Matsuo T. A Study on the Photochemistry of α,β-Unsaturated γ-Lactones. III. Photodimerization of 2-Penten-4-olide. Bull Chem Soc Jpn 1976; 49: 1590-94.

House HO, Ro RS. The Stereochemistry of Base-catalyzed Epoxidation. J Am Chem Soc 1958; 80: 2428-33.

Payne GB, Williams PH. Reactions of Hydrogen Peroxide. VI. Alkaline Epoxidation of Acrylonitrile. J Org Chem 1961; 26: 651-59.

Buckles RE, Mock GV, Locatell L Jr. Toglic And Angelic Acids. Chem Rev 1955; 55: 659-77.

Blatt AH. Pyrolyses of cis-phenyldibenzoylethylene, its oximes and some related heterocyclic compounds. J Org Chem Soc 1950; 15: 869-72.

Blatt AH. Hydroxy Pyrrole Nitrones. II. J Am Chem Soc 1936; 58: 590-94.

Lutz RE, Bailey PS. The Novel Reaction between Amines and Dibenzoylmethylethylene. Evidence for A Chelate Structure for cis-Dibenzoylmethylethylene1. J Am Chem Soc 1945; 67: 2229-32.

Cauzzo G, Mazzucato O, Foffani A. Photochemical Isomerization in Solution Dibenzoyléthyléne and Dibenzoylstyrène. Bull Soc Chim Beiges 1962; 71: 838-44.

Griffin GW, O'Connell EJ. Photochemistry of Dibenzoylethylene; A Novel Photochemical Rearrangement and Reduction. J Am Chem Soc 1962; 84: 4148-49.

Zimmermann HE, Durr HG, Lewis RG et al. Mechanistic Organic Photochemistry. V. Phenyl Migration in a New Photochemical Reaction. J Am Chem Soc 1962; 84: 4149-50.

Zimmerman HE, Durr HG, Givens RS et al. The Photochemistry of Dibenzoylethylenes. Mechanistic and Exploratory Organic Photochemistry. XXII. J Am Chem Soc 1967; 89: 1863–74.

Sugiyama N, Kashima C. The Photoreaction of 1,2-Dibenzoylethylene in Acidic Methanol. Bull Chem Soc Jpn 1970; 43: 1875-77.

Kashima C, Kataoka H, Tanaka K et al. The Photoreaction of p-Substituted β-Benzoylacrylic Acids. Bull Chem Soc Jpn 1970; 43: 1473-77.

Lahiri S, Dabral V, Chauhan SMS et al. Photochemical transformations of cis-1,2-dibenzoylalkenes. J Org Chem1980; 45: 3782–90.

Maji D, Singh R, Mostafa G et al. Topochemical Selectivity in Solid-State Photorearrangement: Conformational Control in Photorearrangements of cis-1,2-Dibenzoylalkenes. J Org Chem 1996; 61: 5165-68.

Pratapan S, Scaria PM, Bhattacharyya K et al. Photochemical transformations of (E)-1-(2'-arylidene-1'-phenylhydrazinyl)-1,2-dibenzoylalkenes. J Org Chem1986; 51: 1972–76.

Kumar CV, Murty BARC, Lahiri S et al. Photochemical transformations and laser flash photolysis studies of dibenzobarrelenes containing 1,2-dibenzoylalkene moieties. J Org Chem 1984; 49: 4923–29.

Murty BARC, Kumar CV, Dabral V et al. Photochemical transformations and laser flash photolysis studies of 1,4- and 1,2-epoxy compounds containing 1,2-dibenzoylalkene moieties. J Org Chem1984; 49: 4165–71.

Ramaiah D, Scaria PM, Cyr DR et al. Phototransformations of benzopyranols and related systems. Steady-state and laser flash photolysis studies. J Org Chem 1988; 53: 2016–22.

Rubin MB, Sander W. The mechanism of photoisomerization of tetrabenzoylethylene. Tetrahedron Lett 1987; 28: 5137-40.

Vadakkan JJ, Raman V, Fernandez NB et al. A novel solvent-assisted domino Michael-aldol reaction of acenaphthenequinone with acetophenones. New J Chem 2003; 27: 239–41.

Jacob AM, Thumpakkara RK, Prathapan S et al. Synthesis of 3,3-dimethoxy-2-aryl-2,3-dihydro-1-oxa-cyclopenta[l]phenanthren-2-ols and their conversion to 2(3H)- and 3(2H)-furanones. Tetrahedron 2005; 61: 4601-07.

Bhattacharya K, Prathapan S, Scaria PM et al. Laser flash photolysis study of (E)-1-(2′-arylidene-1′-phenylhydrazinyl)-1,2-dibenzoylalkenes: Mechanistic aspects of photochemical ring closure. J Photochem1987; 37: 147-57.


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