EtOH/Ba(OH)2 triggers self-condensation of (E)-1,4-diaryl-2- butene-1,4-diones to cyclopentanol derivatives

Synthetic Communications

Volumn 35, Issue 12, 2005, Pages 1707-1714

  Rao, H Surya Prakash ^a   Senthilkumar, S P ^a  

^a PONDICHERRY UNIVERSITY   (India)

Author keywords

1,4 diaryl 2 butene 1,4 diones; Barium hydroxide; Domino reactions

Indexed keywords

2 ETHOXY 3 HYDROXY 4,5 DI(4 METHYLBENZOYL) 3 (4 METHYLPHENYL)CYCLOPENTYL(4 METHYLPHENYL)METHANONE; 4 BROMOPHENYL[4,5 DI(4 BROMOBENZOYL) 3 (4 BROMOPHENYL) 2 ETHOXY 3 HYDROXYCYCLOPENTYL]METHANONE; 4 CHLOROPHENYL[4,5 DI(4 CHLOROBENZOYL) 3 (4 CHLOROPHENYL) 2 ETHOXY 3 HYDROXYCYCLOPENTYL]METHANONE; 4,5 DIBENZOYL 2 ETHOXY 3 HYDROXY 3 PHENYLCYCLOPENTYL(PHENYL)METHANONE; ETHYLENE DERIVATIVE; PENTANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; DOMINO REACTION; POLYMERIZATION; STEREOCHEMISTRY;

EID: 21044456775     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200061715     Document Type: Article

References (17)

1. (a) Kaupp, G.; Poyodda, U.; Atfah, A.; Meier, H.; Vierengel, A. A new reaction type in the conversion of enamines with 1,4-diphenyl-2-butene-1,4-dione to give Cage compounds. Angew. Chem., Int. Ed. Engl. 1992, 31, 768-770;
2. (b) Atfah, M. A.; Al-Arab, M. M. Novel bicyclo[2.2.2]lactones from a facile condensation of dibenzoylethylene with arylacetonitriles. J. Heterocycl. Chem. 1990, 27, 599-603.
3. Tietze, L. F.; Petersen, S. Stereoselective total synthesis of a novel D-homosteroid by a twofold heck reaction. Eur. J. Org. Chem. 2000, 1827-1830.
4. (a) Rao, H. S. P.; Jeyalakshmi, K.; Senthilkumar, S. P. Novel domino products from the reaction of phenyl vinyl ketone and its derivatives with cyclic ketones. Tetrahedron 2002, 58, 2189-2199;
5. (b) Rao, H. S. P.; Jeyalakshmi, K.; Bharathi, B.; Pushpalatha, L.; Uma Maheswari, V. Domino products from the reaction of 1,3-diaryl-2-propen-1-ones (chalcones) with cyclopentanone. J. Indian Chem. Soc. 2001, 78, 787-795.
6. Cabrera, A.; Lagadee, R. L.; Sharma, P.; Arias, J. L.; Toscano, R. A.; Velasco, L.; Gavino, R.; Alvarez, C.; Salman, M. Cyclo- and hydrodimerization of α,β-unsaturated ketones promoted by samarium diiodide. J. Chem. Soc., Perkin Trans. 1 1998, 3609-3518.
7. Al-Arab, M. M.; Atfeh, M. A.; Al-Saleh, F. S. The Michael reaction of acetophenones with trans-dibenzoylethylene. Tetrahedron 1997, 53, 1045-1052.
8. Rao, H. S. P.; Senthilkumar, S. P. Microwave assisted synthesis of phenyl(2-phenyl-5,6,7,8-tetrahydro-4-quinolinyl)methanone and its derivatives. Ind. J. Chem. 2004, 43B, 2426-2430.
9. Lutz, R. E.; Chi-Kang, D. α-Substituted β-diketones. Stereoisomeric enols of α-phenacyldibenzoylmethane. Addition-enolization of unsaturated triketones. J. Org. Chem. 1956, 21, 551-560.
10. Strumza, J.; Altschuler, S. Michael reaction with nitroform and related syntheses. Israel J. Chem. 1963, 1, 106-114;
11. Chemical Abstracts Number (CAN): Strumza, J.; Altschuler, S. Israel J. Chem. 1964, 60:60367.
12. (a) Seko, S.; Miyake, K. Amination of α,β-unsaturated γ-dicarbonyl compounds with methoxyamines. Synth. Commun. 1999, 29, 2487-2492;
13. (b) Tamura, Y.; Sumoto, K.; Matsushima, H.; Taniguchi, H.; Ikda, M. Reactions of N-substituted arylsulfilimines with acylating agents and with activated halobenzenes, alkynes and alkenes. J. Org. Chem. 1973, 38, 4324-4328.
14. Nguyen, V. H.; Nishino, H.; Kurosawa, K. Manganese (III) based facile synthesis of 3-cyano-4,5-dihydrofurans and 4-cyano-1,2-dioxan-3-ols using alkenes and acylacetonitrile building blocks. Synthesis 1997, 8, 899-908.
15. (a) Conant, J. B.; Lutz, R. E. A new method of preparing dibenzoylethylene and related compounds. J. Am. Chem. Soc. 1923, 45, 1303-1307;
16. (b) Campaigne, E.; Foye, W. O. The synthesis of 2,5-diarylthiophenes. J. Org. Chem. 1952, 17, 1405-1412.
17. Garcia-Raso, A.; Garcia-Raso, J.; Campaner, B.; Mestres, R.; Sinistera, J. V. An improved procedure for the Michael reaction of chalcones. Synthesis 1982, 1037-1040.