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Chemical Compound Review

PubChem10849     2,4-bis(4-methoxyphenyl)- 2,4...

Synonyms: AG-H-89677, NSC-150550, AC1L3EQH, ACT09186, AC-16496, ...
 
 
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High impact information on NSC 150550

  • Resin-immobilized beta-ketoamide, aryl-, or alkylhydazine and Lawesson's reagent are suspended in a mixture of THF/Py and heated at 50-55 degrees C to give a resin-bound 5-aminopyrazole, that is liberated from the solid support by treatment with TFA [1].
  • [reaction: see text] Thionation of amides, 1,4-diketones, N-(2-oxoalkyl)amides, N,N'-acylhydrazines, and acyl-protected uridines with the use of a fluorous analogue of the Lawesson's reagent leads to thioamides, thiophenes, 1,3-thiazoles, 1,3,4-thiadiazoles, and acyl-protected 4-thiouridines [2].
  • Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson's reagent-mediated cyclization under microwave irradiation: applications for liquid crystal synthesis [3].
  • [reactions: see text] An expeditious, solvent-free, and high yield conversion of ketones, flavones, isoflavones, lactones, amides, and esters to the corresponding thio analogues is described utilizing Lawesson's reagent in a process that circumvents the use of dry solvents and excess of the reagent [4].
  • Alkaline hydrolysis (NaOH) followed by acidification (KHSO4) or thioamide formation (Lawsson's Reagent, C.A.S. 19172-47-5), afforded the corresponding free acids IIIa-d or the thioamides IVa-d respectively [5].
 

Anatomical context of NSC 150550

 

Analytical, diagnostic and therapeutic context of NSC 150550

  • The method has the advantage that reagent-derived byproducts may be removed by a simple hydrolytic workup or by filtration through silica gel, rather than by chromatography, as required for Lawesson's reagent [7].

References

  1. Solid-phase synthesis of 5-substituted amino pyrazoles. Dodd, D.S., Martinez, R.L., Kamau, M., Ruan, Z., Van Kirk, K., Cooper, C.B., Hermsmeier, M.A., Traeger, S.C., Poss, M.A. Journal of combinatorial chemistry. (2005) [Pubmed]
  2. Thionation using fluorous Lawesson's reagent. Kaleta, Z., Makowski, B.T., Soós, T., Dembinski, R. Org. Lett. (2006) [Pubmed]
  3. Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson's reagent-mediated cyclization under microwave irradiation: applications for liquid crystal synthesis. Kiryanov, A.A., Sampson, P., Seed, A.J. J. Org. Chem. (2001) [Pubmed]
  4. Microwave-accelerated solvent-free synthesis of thioketones, thiolactones, thioamides, thionoesters, and thioflavonoids. Varma, R.S., Kumar, D. Org. Lett. (1999) [Pubmed]
  5. Synthesis and anti-phlogistic potency of some new non-proteinogenic amino acid conjugates of "Diclofenac". Abo-Ghalia, M.H., Shalaby, A.M., el-Eraqi, W.I., Awad, H.M. Amino Acids (1999) [Pubmed]
  6. Hydrogen sulfide is an endogenous modulator of leukocyte-mediated inflammation. Zanardo, R.C., Brancaleone, V., Distrutti, E., Fiorucci, S., Cirino, G., Wallace, J.L. FASEB J. (2006) [Pubmed]
  7. Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane. Curphey, T.J. J. Org. Chem. (2002) [Pubmed]
 
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