Water-Promoted Synthesis of Enaminones: Mechanism Investigation and Application in Multicomponent Reactions

REFERENCES

• Reddy , G. J. ; Latha , D. ; Thirupathaiah , C. ; Rao , K. S. A facile synthesis of 2,3-disubstituted-6-arylpyridines from enaminones using montmorillonite K10 as solid acid support . Tetrahedron Lett. 2005 , 46 , 301 – 302 .
   Web of Science ®Google Scholar
• Wang , G. W. ; Miao , C. B. Environmentally benign, one-pot, multicomponent approaches to the synthesis of novel unsymmetrical 4-arylacridinediones . Green Chem. 2006 , 8 , 1080 – 1085 .
   Web of Science ®Google Scholar
• Wang , M. ; Liu , Y. ; Gao , H. ; Zhang , Y. ; Yu , C. ; Huang , Z. ; Fleet , G. W. J. Ring-chain tautomerism in organic synthesis: Synthesis of heterocyclic enamines from a novel and practical formal ring transformation reaction of lactones . J. Org. Chem. 2003 , 68 , 3281 – 3286 .
   PubMed Web of Science ®Google Scholar
• Boger , D. L. ; Ishizaki , T. ; Wysocki , R. J. ; Munk , S. A. ; Kitos , P. A. ; Suntornwat , O. Total synthesis and evaluation of (±)-N-(tert-butyloxycarbonyl)-cbi, (±)-cbi-cdpi1, and (±)-cbi-cdpi2-cc-1065 functional agents incorporating the equivalent 1,2,9,9a-tetrahydrocycloprop[1,2-c]benz[1,2-e]indol-4-one (cbi) left-hand subunit . J. Am. Chem. Soc. 1989 , 111 , 6461 – 6463 .
   Web of Science ®Google Scholar
• Wan , J.-P. ; Liu , Y. Synthesis of dihydropyrimidinones and thiones by multicomponent reactions: Strategies beyond the classical Biginelli reaction . Synthesis 2010 , 3943 – 3953 .
   Web of Science ®Google Scholar
• Yang , J. ; Wang , C. ; Xie , X. ; Li , H. ; Li , Y. Acid-catalyzed cascade reactions of enaminones with aldehydes: C-H functionalization to afford 1,4-dihydropyridines . Eur. J. Org. Chem. 2010 , 4189 – 4193 .
   Web of Science ®Google Scholar
• Zang , H. ; Gates , K. S. DNA binding and alkylation by the “left half” of azinomycin B . Biochemistry 2000 , 39 , 14968 – 14975 .
   PubMed Web of Science ®Google Scholar
• Foster , J. E. ; Nicholson , J. M. ; Butcher , R. ; Stables , J. P. ; Edafiogho , I. O. ; Goodwin , A. M. ; Henson , M. C. ; Smith , C. A. ; Scott , K. R. Synthesis, characterization, and anticonvulsant activity of enaminones, part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants . Bioorg. Med. Chem. 1997 , 7 , 2415 – 2425 .
   Web of Science ®Google Scholar
• Eddington , N. D. ; Cox , D. S. ; Roberts , R. R. ; Stables , J. P. ; Powell , C. B. ; Scott , K. R. Enaminones—Versatile therapeutic pharmacophores: Further advances . Curr. Med. Chem. 2007 , 7 , 417 – 436 .
   Web of Science ®Google Scholar
• Stanovnik , B. ; Svete , J. Synthesis of heterocycles from alkyl 3-(dimethylamino)propenoates and related enaminones . Chem. Rev. 2004 , 104 , 2433 – 2480 .
   PubMed Web of Science ®Google Scholar
• Elassar , A. Z. A. ; EI-Khair , A. A. Recent developments in the chemistry of enaminones . Tetrahedron 2003 , 59 , 8463 – 8480 .
   Web of Science ®Google Scholar
• Valduga , C.-J. ; Squizani , A. ; Braibante , H. S. ; Braibante , M. E. F. The use of K-10/ultrasound in the selective synthesis of unsymmetrical beta-enamino ketones . Synthesis 1998 , 1019 – 1022 .
   Web of Science ®Google Scholar
• Rafiee , E. ; Joshaghani , M. ; Eavani , S. ; Rashidadeh , S. A revision for the synthesis of β-enaminones in solvent-free conditions: Efficacy of different supported heteropoly acids as active and reusable catalysts . Green Chem. 2008 , 10 , 982 – 989 .
   Web of Science ®Google Scholar
• Zhao , Y. ; Zhao , J. ; Zhou , Y. ; Lei , Z. ; Li , L. ; Zhang , H. Efficient synthesis of β-amino-α, β-unsaturated carbonyl compounds . New. J. Chem. 2005 , 29 , 769 – 772 .
   Web of Science ®Google Scholar
• Brandt , C. A. ; Da Silva , A. C. M. P. ; Pancote , C. G. ; Brito , C. L. ; Da Silveira , M. A. B. Efficient synthetic method for β-enamino esters using ultrasound . Synthesis 2004 , 1557 – 1559 .
   Web of Science ®Google Scholar
• El-Taweel , F. M. A. A. ; Elnagdi , M. H. Studies with enaminones: Synthesis of new coumarin-3-yl azoles, coumarin-3-yl azines, coumarin-3-yl azoloazines, coumarin-3-yl pyrone and coumarin-2-yl benzo[b]furans . J. Heterocycl. Chem. 2001 , 38 , 981 – 984 .
   Web of Science ®Google Scholar
• Thorwirth , R. ; Stolle , A. Solvent-free synthesis of enamines from alkyl esters of propiolic or but-2-yne dicarboxylic acid in a ball mill . Synlett 2011 , 2200 – 2202 .
   Web of Science ®Google Scholar
• Um , I.-H. ; Lee , E.-J. ; Seok , J.-A. ; Kim , K. H. The α-effect in reactions of sp-hybridized carbon atom: Michael-type reactions of 1-aryl-2-propyn-1-ones with primary amines. J. Org. Chem. 2005, 70, 7530–2536.
   PubMed Web of Science ®Google Scholar
• Azizian , J. ; Hatamjafari , F. ; Karimi , A. R. ; Shaabanzadeh , M. Multicomponent reaction of amines, alkyl propiolates, and ninhydrin: An efficient protocol for the synthesis of tetrahydro-dihydroxy-oxoindeno[1,2-b]pyrrole derivatives . Synthesis 2006 , 765 – 767 .
   Web of Science ®Google Scholar
• Wang , Y. ; Bi , X. ; Li , W. ; Li , D. ; Zhang , Q. ; Liu , Q. ; Ondon , B. Iron-catalyzed aminolysis of β-carbonyl 1,3-dithianes: synthesis of stereodefined β-enaminones and 3,4-disubstituted pyrazoles . Org. Lett. 2011 , 13 , 1722 – 1725 .
   PubMed Web of Science ®Google Scholar
• Wan , J.-P. ; Pan , Y.-J. Chemo-/regioselective synthesis of 6-unsubstituted dihydropyrimidinones, 1,3-thiazines and chromones via novel variants of Biginelli reaction . Chem. Commun. 2009 , 2768 – 2770 .
   PubMed Web of Science ®Google Scholar
• Wan , J.-P. ; Gan , S.-F. ; Sun , G.-L. ; Pan , Y.-J. Novel regioselectivity: three-component cascade synthesis of unsymmetrical 1,4-and 1,2-dihydropyridines . J. Org. Chem. 2009 , 74 , 2862 – 2865 .
   PubMed Web of Science ®Google Scholar
• Wan , J.-P. ; Wang , C. ; Pan , Y. Novel four-component reaction towards diastereoselective synthesis of tetrahydropyrimidinthiones . Tetrahedron 2011 , 67 , 922 – 926 .
   Web of Science ®Google Scholar
• Al-Saleh , B. ; El-Apasery , M. A. ; Abdel-Aziz , R. S. ; Elnagdi , M. H. Enaminones in heterocyclic synthesis: Synthesis and chemical reactivity of 3-anilino-1-substituted-2-propene-1-one . J. Heterocyclic Chem. 2005 , 42 , 563 – 566 .
   Web of Science ®Google Scholar