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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 1
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Original Articles

Facile Microwave-Assisted Michael Addition of Diphenacyl Sulfides to Chalcones Under Solvent-Free Conditions: Generation of Symmetrical and Unsymmetrical 1,5-Diketones

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Pages 129-138 | Received 22 Apr 2011, Published online: 05 Sep 2012

REFERENCES

  • For examples of Michael addition of enolates, see (a) Tozawa , T. ; Yamane , Y. ; Mukaiyama , T. Enantioselective synthesis of 3,4-dihydropyran-2-ones by chiral quaternary ammonium phenoxide–catalyzed tandem Michael addition and lactonization . Chem. Lett. 2006 , 35 , 56 – 57 ; (b) Takenaka , N. ; Abell , J. P. ; Yamamoto , H. Asymmetric conjugate addition of silyl enol ethers catalyzed by tethered bis(8-quinolinolato) aluminum complexes . J. Am. Chem. Soc. 2007 , 129 , 742 – 743 ; (c) Wang , W. ; Li , H. ; Wang , J. Enantioselective organocatalytic Mukaiyama−Michael addition of silyl enol ethers to α, β-unsaturated aldehydes . Org. Lett. 2005 , 7 , 1637 – 1639 ; (d) Tozawa , T. ; Yamane , Y. ; Mukaiyama , T. Diastereo- and enantioselective tandem Michael addition and lactonization between silyl enolates and α,β-unsaturated ketones catalyzed by a chiral quaternary ammonium phenoxide . Chem. Lett. 2006 , 35 , 360 – 361 ; (e) Nakagawa , T. ; Fujisawa , H. ; Nagata , Y. ; Mukaiyama , T. Lewis base–catalyzed Michael reactions between trimethylsilyl enolate and α,β-unsaturated carbonyl compounds . Bull. Chem. Soc. Jpn. 2005 , 78 , 236 – 246 ; (f) Liu , D. ; Hong , S. ; Corey , E. J. Enantioselective synthesis of bridged- or fused-ring bicyclic ketones by a catalytic asymmetric Michael addition pathway . J. Am. Chem. Soc. 2006 , 128 , 8160 – 8161 ; For reviews, see (g) Heathcock , C. H. Comprehensive Organic Synthesis; B. M. Trost, I. Fleming, C. H. Heathcock (Eds.); Pergamon: Oxford, UK, 1991; vol. 2, p. 133; (h) Jung , M. E. Comprehensive Organic Synthesis; B. M. Trost, I. Fleming, M. F. Semmelhack (Eds.); Pergamon: Oxford, UK, 1991; vol. 4, p. 1 .
  • (a) Ariyan , Z. S. ; Suschitzky , H. Heterocyclic compounds of the chalcone type. J. Chem Soc. 1961, 2242–2244; (b) Hirsch , S. S. ; Bailey , W. J. Base-catalyzed alkylation of cyclopentadiene rings with alcohols and amines. J. Org. Chem. 1978, 43, 4090–4094; (c) Krohnke , F. The specific synthesis of pyridines and oligopyridines. Synthesis 1976, 1–24; (d) 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, 4923–4928; (e) Bagrina , N. P. ; Vysotskii , V. I. ; Sergeeva , S. A. ; Denisenko , V. A. ; Gerasimenko , A. V. Acid-catalyzed condensation of 1,3,5-triphenylpentane-1,5-dione with benzaldehyde—A new domino reaction. Russ. J. Org. Chem. 2004, 40, 479–481.
  • (a) Takahashi , H. ; Arai , T. ; Yanagisawa , A. 1,5-Diketone synthesis promoted by barium hydride or barium alkoxides . Synlett 2006 , 2833 – 2835 ; (b) Yanagisawa , A. ; Takahashi , H. ; Arai , T. One-pot synthesis of 1,5-diketones catalyzed by barium isopropoxide . Tetrahedron 2007 , 63 , 8581 – 8585 .
  • Ceylan , M. ; Gezegen , H. Preparation of 1,5-diketones by addition of cyclohexanone to chalcones under solvent-free phase-transfer catalyst condition . Turk. J. Chem. 2008 , 32 , 55 – 61 .
  • Swamy , V. M. ; Sarkar , A. Alkali metal hydride– or aqueous hydroxide–induced conjugate addition of trimethylsilyl enol ethers to enones: A convenient alternative to Lewis acid–mediated reaction . Tetrahedron Lett. 1998 , 39 , 1261 – 1264 .
  • 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 – 1848 .
  • (a) Jha , S. C. ; Joshi , N. N. Catalytic, enantioselective Michael addition reactions . Arkivoc 2002 , 167 – 196 ; (b) Sibi , M. P. ; Manyem , S. Enantioselective conjugate additions . Tetrahedron 2000 , 56 , 8033 – 8061 ; (c) Paul , S. ; Gupta , M. ; Singh , P. ; Gupta , R. ; Loupy , A. A mild, efficient, and green procedure for Michael addition of active methylene compounds to chalcones under microwave irradiation . Synth. Commun. 2005 , 35 , 325 – 332 .
  • (a) Caddick , S. Microwave-assisted organic reactions . Tetrahedron 1995 , 51 , 10403 – 10432 ; (b) Strauss , C. R. ; Trainor , R. W. Developments in microwave-assisted organic chemistry . Aust. J. Chem. 1995 , 48 , 1665 – 1692 ; (c) Larhed , M. ; Moberg , C. ; Hallberg , A. Microwave-accelerated homogeneous catalysis in organic chemistry . Acc. Chem. Res. 2002 , 35 , 717 – 727 .
  • (a) Toda , F. Solid state organic chemistry: Efficient reactions, remarkable yields, and stereoselectivity . Acc. Chem. Res. 1995 , 28 , 480 – 486 ; (b) 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 – 1909 ; (c) 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 , 719 , 637 – 639 ; (d) 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 – 3933 .
  • For reviews concerning the combinatorial use of microwave irradiation 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 – 55 ; (b) Varma , R. S. Solvent-free accelerated organic syntheses using microwaves . Pure Appl. Chem. 2001 , 73 , 193 – 198 ; (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 – 1234 .
  • (a) Ponpandian , T. ; Muthusubramanian , S. A new method of synthesising (±)-thalictroidine and (±)-hygrine. Tetrahedron Lett. 2011, 52, 1520–1522; (b) Ravindran , G. ; Muthusubramanian , S. ; Selvaraj , S. ; Perumal , S. Synthesis of 1,2,3,4,5-pentasubstituted symmetrical pyrroles. Arkivoc 2007, 13, 23–27; (c) Sridharan , V. ; Muthusubramanian , S. ; Sivasubramanian , S. ; Polborn , K. Diastereoselective synthesis of 2,3,4,5-tetrasubstituted isoxazolidines via 1,3-dipolar cycloaddition. Tetrahedron 2004, 60, 8881–8892; (d) Saravanan , S. ; Azath , I. A. ; Muthusubramanian , S. Synthesis of highly substituted 2,3-dihydro-1H-pyrrole derivatives via a tandem regioselective addition of nitrones to 1,3-enynes with subsequent rearrangement. J. Org. Chem. 2008, 73, 2323–2329.
  • Paul , N. ; Muthusubramanian , S. Domino Vilsmeier–Haack/ring-closure sequences: A facile synthesis of 3-chlorobenzo[b]thiophene-2-carbaldehydes . Tetrahedron Lett. 2011 , 52 , 3743 – 3746 .
  • Ravindran , G. ; Muthusubramanian , S. ; Perumal , S. A convenient one-pot synthesis of highly substituted piperidines through a Michael addition–aldol cyclization sequence . Arkivoc 2008 , 13 , 57 – 64 .
  • Ravindran , G. ; Paul , N. ; Muthusubramanian , S. ; Perumal , S. Synthesis of 2,5-diaroyl-3-arylthiophenes: Novel tandem reactions mediated [3 + 2]-self annulation of bis(aroylmethyl)sulfides . J. Sulfur Chem. 2008 , 29 , 575 – 581 .
  • Takeda , M. ; Hashimoto , T. ; Fujii , T. ; Ono , S. ; Yoshimura , T. ; Shimasaki , C. ; Morita , H. 2-Benzothiazolyl phenacyl sulfoxide, a new precursor of 2-oxo-2-phenylethanethial . Heteroatom Chem. 1999 , 10 , 363 – 367
  • Rao , H. S. P. ; Jothilingam , S. Solvent-free microwave-mediated Michael addition reactions . J. Chem. Sci. 2005 , 117 , 323 – 328 .

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