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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 6
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Original Articles

Microwave-Assisted Michael Addition of Diethyl Malonate with Ferrocenyl Substituted Chalcones Under Solvent-Free Conditions

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Pages 851-857 | Received 27 May 2008, Published online: 25 Feb 2011

REFERENCES

  • (a) Ariyan , Z. S. ; Suschitzky , H. Heterocyclic compounds of the chalcone type . J. Chem. Soc. 1961 , 2242 ; (b) Hirsch , S. S. ; Bailey , W. J. Base-catalyzed alkylation of cyclopentadiene rings with alcohols and amines . J. Org. Chem. 1978 , 43 , 4090 ; (c) Krohnke , F. The specific synthesis of pyridines and oligopyridines . Synthesis 1976 , 1 ; (d) Constable , E. C. ; Thompson , A. M. W. C. Ligand reactivity in iron(II) complexes of 4′-(4‴-pyridyl)-2,2′:6′,2″-terpyridine . J. Chem. Soc., Dalton Trans. 1992 , 2947 ; (e) Potts , K. T. α,α′-Oligopyridines: A source of new materials . Bull. Soc. Chem. Belg. 1990 , 99 , 741 ; (f) Butler , I. R. ; McDonald , S. J. Ferrocenylpyridines: A new synthesis of 4′-ferrocenylterpyridine and the single-crystal structure of a C3-ferrocenophane, [(η-C5H4CHCH2C(O)2-C5H4N)2CHC(O)2-C5H4N]Fe . Polyhedron 1995 , 14 , 529 ; (g) Gill , N. S. ; James , K. B. ; Lions , F. ; Potts , K. T. β-Acylethylation with ketonic Mannich bases: The synthesis of some diketones, ketonic sulfides, nitro ketones, and pyridines . J. Am. Chem. Soc. 1952 , 74 , 4923 .
  • For reviews, see (a) Bergmann , E. D. ; Ginsburg , D. ; Pappo , R. The Michael reaction . Org. React. 1959 , 10 , 179 ; (b) Perlmutter , P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992 ; (c) Vicario , J. L. ; Badia , D. ; Carrillo , L. Organocatalytic enantioselective Michael and hetero-Michael reactions . Synthesis 2007 , 2065 ; (d) Christoffers , J. ; Koripelly , G. ; Rosiak , A. ; Roessle , M. Recent advances in metal-catalyzed asymmetric conjugate additions . Synthesis 2007 , 1279 ; (e) Tsogoeva , S. B. Recent advances in asymmetric organocatalytic 1,4-conjugate additions . Eur. J. Org. Chem. 2007 , 1701 ; (f) Almasi , D. ; Alonso , D. A. ; Najera , C. Organocatalytic asymmetric conjugate additions . Tetrahedron: Asymmetry 2007 , 18 , 299 ; (g) Jha , S. C. ; Joshi , N. N. Catalytic, enantioselective Michael addition reactions . Arkivoc 2002 , 167 ; (h) Sibi , M. P. ; Manyem , S. Enantioselective conjugate additions . Tetrahedron 2000 , 56 , 8033 .
  • Rapic , V. ; Lasinger , J. Ferrocene compounds, XIV: Synthesis and reactions of 3-aryl-5-ferrocenyl-5-oxovaleric acids . Croat. Chem. Acta 1985 , 58 , 315 .
  • Kaluz , S. ; Toma , S. Addition of C- and S-nucleophiles to acryloylferrocene and cinnamoylferrocene catalyzed by potassium fluoride–alumina . Collect. Czech. Chem. Commun. 1986 , 51 , 2199 .
  • For recent reviews on microwave-assisted chemical reactions, see (a) Caddick , S. Microwave-assisted organic reactions . Tetrahedron 1995 , 51 , 10403 ; (b) Strauss , C. R. ; Trainor , R. W. Developments in microwave-assisted organic chemistry . Aust. J. Chem. 1995 , 48 , 1665 ; (c) Larhed , M. ; Moberg , C. ; Hallberg , A. Microwave-accelerated homogeneous catalysis in organic chemistry . Acc. Chem. Res. 2002 , 35 , 717 . For selected examples, see (d) Tu , S. J. ; Li , C. M. ; Shi , F. ; Zhou , D. X. ; Shao , Q. Q. ; Cao , L. J. ; Jiang , B. An efficient chemoselective synthesis of pyrido[2,3-d]pyrimidine derivatives under microwave irradiation . Synthesis 2008 , 369 ; (e) Tu , S. J. ; Shao , Q. Q. ; Zhou , D. X. ; Cao , L. J. ; Shi , F. ; Li , C. M. Microwave-assisted efficient synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine derivatives in water under catalyst-free conditions . J. Heterocycl. Chem. 2007 , 44 , 1401 ; (f) Tu , S. J. ; Li , C. M. ; Li , G. G. ; Cao , L. J. ; Shao , Q. Q. ; Zhou , D. X. ; Jiang , B. ; Zhou , J. F. ; Xia , M. Microwave-assisted combinatorial synthesis of polysubstituent imidazo[1,2-a]quinoline, pyrimido[1,2-a]quinoline, and quinolino[1,2-a]quinazoline derivatives . J. Comb. Chem. 2007 , 9 , 1144 ; (g) Jin , T. S. ; Zhang , F. S. ; Wang , K. F. ; Li , T. S. Synthesis of pentaerythritol diacetals from aldehydes and ketones under microwave irradiation . Chin. J. Org. Chem. 2004 , 24 , 1485 ; (h) Jin , T. S. ; Wang , H. X. ; Wang , K. F. ; Li , T. S. Synthesis of diacetals from aldehydes and ketones with pentaerythritol catalyzed by silica sulfate under microwave irradiation . Synth. Commun. 2004 , 34 , 2993 .
  • For reviews, see (a) Toda , F. Solid state organic chemistry: Efficient reactions, remarkable yields, and stereoselectivity. Acc. Chem. Res. 1995, 28, 480; (b) Tanaka , K. ; Toda , F. Solvent-free organic synthesis. Chem. Rev. 2000, 100, 1025. For selected examples, see (c) Ji , S.-J. ; Shen , Z.-L. ; Gu , D.-G. ; Huang , X.-Y. Ultrasound-promoted alkynylation of ethynylbenzene to ketones under solvent-free condition. Ultrason. Sonochem. 2005, 12, 161; (d) Shen , Z.-L. ; Ji , S.-J. ; Loh , T.-P. An environmentally friendly procedure for Mukaiyama aldol and Mukaiyama–Michael reactions using a catalytic amount of DBU under solvent- and metal-free conditions. Tetrahedron Lett. 2005, 3, 507; (e) Shen , Z.-L. ; Ji , S.-J. ; Zhou , W.-J. Efficient and environmentally friendly approach to the synthesis of ferrocenyl-substituted 1,5-diketone compounds under solvent-free conditions. Synth. Commun. 2005, 35, 1903; (f) Liu , W.-Y. ; Xu , Q.-H. ; Liang , Y.-M. ; Chen , B.-H. ; Liu , W.-M. ; Ma , Y.-X. Preparation of 1,5-diketone derivatives containing ferrocenyl by Michael reaction under solvent-free condition. J. Organomet. Chem. 2001, 637–639, 719; (g) Rong , L. C. ; Han , H. X. ; Jiang , H. ; Shi , D. Q. ; Tu , S. J. One-pot synthesis of 4,6-diaryl-2-oxo-1,2-dihydropyridine-3-carbonitriles via three-component cyclocondensation under solvent-free conditions. Synth. Commun. 2008, 38, 217; (h) Wang , X. S. ; Zhang , M. M. ; Jiang , H. ; Yao , C. S. ; Tu , S. J. Uncatalyzed and solvent-free process for the synthesis of 1,4-diarylquinoline derivatives. Synth. Commun. 2008, 38, 1355; (i) Yang , J. M. ; Ji , S. J. ; Gu , D. G. ; Shen , Z. L. ; Wang , S. Y. Ultrasound-irradiated Michael addition of amines to ferrocenylenones under solvent-free and catalyst-free conditions at room temperature. J. Organomet. Chem. 2005, 690, 2989; (j) Jin , T. S. ; Zhang , J. S. ; Wang , A. Q. ; Li , T. S. Solid-state condensation reactions between aldehydes and 5,5-dimethyl-1,3-cyclohexanedione by grinding at room temperature. Synth. Commun. 2005, 35, 2339; (k) Shen , Z.-L. ; Zhou , W.-J. ; Yang , J.-M. ; Ji , S.-J. Efficient synthesis of ferrocenylcyclohexenone under solvent-free conditions. Synth. Commun. 2009, 39, 3924.
  • For reviews concerning the combinatorial use of MWI and solvent-free conditions in organic reactions, see (a) Varma , R. S. Solvent-free organic syntheses using supported reagents and microwave irradiation . Green Chem. 1999 , 1 , 43 ; (b) Varma , R. S. Solvent-free accelerated organic syntheses using microwaves . Pure Appl. Chem. 2001 , 73 , 193 ; (c) Loupy , A. ; Petit , A. ; Hamelin , J. ; Texier-Boullet , F. ; Jacquault , P. ; Mathe , D. New solvent-free organic synthesis using focused microwaves . Synthesis 1998 , 1213 . For selected examples, see (d) Jin , T. S. ; Feng , G. L. ; Yang , M. N. ; Li , T. S. A solvent-free procedure for synthesis of N-sulfonylimines using microwave irradiation catalyzed by ZrO2/ solid superacid . Synth. Commun. 2004 , 34 , 1277 ; (e) Ji , S.-J. ; Lu , J. ; Zhu , X. ; Yang , J. ; Lang , J.-P. ; Wu , L. Microwave-assisted efficient oxidative coupling of 2-naphthols in the solid state . Synth. Commun. 2002 , 32 , 3069 ; (f) Tu , S.-J. ; Wei , Q.-H. ; Ma , H.-J. ; Shi , D.-Q. ; Gao , Y. ; Cui , G.-Y. The synthesis of novel substituted 2,5-dioxo-1,2,3,4,5,6,7,8-octahydroquinolines without solvent under microwave irradiation . Synth. Commun. 2001 , 31 , 2657 ; (g) Feng , J.-C. ; Liu , B. ; Liu , Y. ; Li , C.-C. An efficient one-pot synthesis of nitriles from carboxylic acids without solvent under microwave irradiation . Synth. Commun. 1996 , 26 , 4545 .
  • Tirouflet , J. ; Boichard , J. ; Metallocenes , I. Imines and chalcones derived from ferrocenecarboxaldehyde and acetylferrocene . Bull. Soc. Chim. Fr. 1963 , 851 .
  • (a) Ji , S. J. ; Shen , Z. L. ; Wang , S. Y. Aldol condensation of acetylferrocene under ultrasound . Chin. Chem. Lett. 2003 , 14 , 663 ; (b) Ji , S.-J. ; Shen , Z.-L. ; Gu , D.-G. ; Wang , S.-Y. An efficient synthesis of ferrocenyl substituted 1,5-diketone and cyclic α,β-unsaturated ketones under ultrasound irradiation . J. Organomet. Chem. 2004 , 689 , 1843 .
  • Melot , J. M. ; Texier-Boullet , F. ; Foucaud , A. Cyclopropanation of electrophilic alkenes with nitroalkanes in the presence of alumina-supported potassium fluoride . Synthesis 1987 , 364 .

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