HTIB-Mediated One-Pot Synthesis of Some 2-Substituted 4-Styrylthiazoles from (E)-4-Arylbut-3-en-2-ones

REFERENCES

• Haddow , A. ; Haris , R. J. C. ; Kon , G. A. R. ; Roe , E. M. F. The growth inhibitory and carcinogenic properties of 4-aminostilbene and derivatives . Trans. Royal Soc. A (London) 1948 , 241 , 147 .
   Web of Science ®Google Scholar
• Alajarin , M. ; Cabrera , J. ; Pastor , A. ; Sanchez-Andrada , P. ; Bautista , D. Diels–Alder reactions of 4-alkenylthiazoles: A new approach to thiazole functionalization . J. Org. Chem. 2007 , 72 , 2097 .
   PubMed Web of Science ®Google Scholar
• Alajarin , M. ; Cabrera , J. ; Pastor , A. ; Sanchez-Andrada , P. ; Bautista , D. Polar hetero-Diels–Alder reactions of 4-alkenylthiazoles with 1,2,4-triazoline-3,5-diones: An experimental and computational study . J. Org. Chem. 2008 , 73 , 963 .
   PubMed Web of Science ®Google Scholar
• Moody , C. J. ; Bagley , M. C. Total synthesis of (+)-nostocyclamide . J. Chem. Soc., Perkin Trans. 1 1998 , 601 .
   Google Scholar
• Moody , C. J. Addition reactions of ROPHy/SOPHy oxime ethers: Asymmetric synthesis of nitrogen-containing compounds . Chem. Commun. 2004 , 1341 .
   Web of Science ®Google Scholar
• Southwick , P. L. ; Sapper , D. I. 4-Styrylthiazoles: Syntheses and relationships among ultraviolet absorption spectra . J. Org. Chem. 1954 , 19 , 1926 .
   Web of Science ®Google Scholar
• (a) Moriarity , R. M. ; Prakash , O. Advances in Heterocyclic Chemistry ; A. R. Katritzky (Ed.); Academic Press : Chicago , 1998 ; vol 1 , p. 69 ; (b) Prakash , O. ; Saini , N. ; Sharma , P. K. [Hydroxy(tosyloxy)iodo]benzene: A useful hypervalent iodine reagent for the synthesis of heterocyclic compounds. Heterocycles 1994, 38, 409; (c) Koser , G. F. The synthesis of heterocyclic compounds with hypervalent organoiodine reagents. Advances in Heterocyclic Chemistry, 2004, 86, 225 .
   Google Scholar
• (a) Prakash , O. ; Rani , N. ; Goyal , S. Hypervalent iodine in the synthesis of bridgehead heterocycles: novel and facile syntheses of 3-substituted-5,6-dihydroimidazo[2,1-b]thiazoles and 3-phenylthiazolo[3,2-a]benzimidazole from acetophenones using [hydroxy(tosyloxy)iodo]benzene. J. Chem. Soc. Perkin Tran 1 1992, 707; (b) Prakash , O. ; Batra , A. ; Chaudhri , V. ; Prakash , R. Use of [hydroxy(tosyloxy)iodo]benzene in a novel and facile synthesis of 1,4-diaryl-2-(arylamino)but-2-ene-1,4-diones. Tetrahedron Lett. 2005, 46, 2877; (c) Kumar , R. [hydroxy(tosyloxy)iodo]benzene. Synlett 2007, 2764; (d) Prakash , O. ; Kumar , R. ; Sharma , D. ; Pannu , K. ; Kamal , R. The chemistry of α, β-ditosyloxyketones: Novel routes for the synthesis of desoxybenzoins and α-aryl-β-ketoaldehyde dimethylacetals from α, β-chacone ditosylates. Synlett 2007, 2189; (e) Prakash , O. ; Pannu , K. ; Prakash , R. ; Batra , A. [hydroxy(tosyloxy)iodo]benzene mediated α-azidation of ketones. Molecules 2006, 11, 523; (f) Aggarwal , R. ; Pundeer , R. ; Kumar , V. ; Chaudhri , V. ; Singh , S. P. ; Prakash , O. A facile synthesis of thiazole-2(3H)-thiones through [hydroxy(tosyloxy)iodo]benzene. Synth. Commun. 2004, 34, 2659; (g) Prakash , O. ; Pundeer , P. ; Chaudhri , V. Organoiodine (III) mediated one-pot synthesis of n-substituted 2-aminothiazoles. J. Ind. Chem. Soc. 2004, 786; (h) Singh , S. P. ; Naithani , R. ; Prakash , O. A facile [hydroxy(tosyloxy)iodo]benzene-mediated synthesis of substituted imidazo (1,2-a)-pyridines. J. Ind. Chem. Soc. 1998, 75, 770.
   Google Scholar
• Kumar , D. ; Sundaree , M. S. ; Patel , G. ; Rao , V. S. ; Varma , R. S. Solvent-free facile synthesis of novel α-tosyloxy-β-keto sulphones using [hydroxy(tosyloxy)iodo]benzene . Tetrahedron Lett. 2006 , 47 , 8239 .
   Web of Science ®Google Scholar
• Xie , Y. Y. ; Chen , Z. C. Hypervalent iodine in synthesis: One-pot preparation of β-keto sulfones by the reaction of ketones, [hydroxy(tosyloxy)iodo]benzene, and sulfinates . Synth. Commun. 2001 , 31 , 3145 .
   Web of Science ®Google Scholar
• Zhou , G. B. ; Guan , Y. Q. ; Shen , C. ; Wang , Q. ; Liu , X. M. ; Zhang , P. F. ; Li , L. L. A novel and convenient synthesis of thiazol-2(3H)-imine-linked glycoconjugates . Synthesis 2008 , 13 , 1994 .
   Web of Science ®Google Scholar
• Karade , N. ; Tiwari , G. B. ; Gampawar , S. V. ; Shinde , S. V. Convenient synthesis of symmetrical diketosulfides from enolizable ketones using [hydroxy(tosyloxy)iodo]benzene and Na2S · 9H2O . Heteroatom Chem. 2009 , 20 , 172 .
   Web of Science ®Google Scholar
• Koser , G. F. ; Relenyi , A. G. ; Kalos , A. N. ; Rebrovic , L. ; Wettach , R. H. One-step α-tosyloxylation of ketones with [hydroxy(tosyloxy)iodo]benzene . J. Org. Chem. 1982 , 47 , 2487 .
   Web of Science ®Google Scholar
• Prakash , O. ; Sharma , N. ; Ranjan , P. [Hydroxy(tosyloxy)iodo]benzene: A tosyloxylating agent with selectivity for ketones in the reactions with benzalacetones . Synth. Commun. 2010 , 40 , 2875 .
   Web of Science ®Google Scholar
• Rout , M. K. ; Ravenshaw , C. ; Cuttack . Condensation products of benzylideneacetone with substituted thioureas . J. Ind. Chem. Soc. 1956 , 33 , 796 .
   Google Scholar