Rapid and efficient diazotization and diazo coupling reactions on silica sulfuric acid under solvent-free conditions

Dyes and Pigments

Volumn 81, Issue 3, 2009, Pages 240-244

  Zarei, Amin ^a   Hajipour, Abdol R ^b,c   Khazdooz, Leila ^c   Mirjalili, Bibi F ^d   Najafi Chermahini, Alireza ^e  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

^c ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^d YAZD UNIVERSITY   (Iran)

^e University of Yasuoj   (Iran)

Author keywords

Azo dyes; Diazo coupling; Diazotization; Silica sulfuric acid; Solvent free conditions

Indexed keywords

ACIDS; AMINES; AROMATIC COMPOUNDS; AZO DYES; COUPLING AGENTS; ORGANIC COMPOUNDS; OXIDES; SILICA; SILICON COMPOUNDS; SOLVENTS; SULFUR DETERMINATION;

AROMATIC AMINES; ARYLDIAZONIUM SALTS; COUPLING REACTIONS; DIAZO COUPLING; DIAZOTIZATION; DRY STATES; GOOD YIELDS; MILD REACTION CONDITIONS; ONE POTS; ROOM TEMPERATURES; SILICA SULFURIC ACID; SUPPORTED ON SILICAS; SYNTHESIS OF;

SULFURIC ACID;

AMINE; AZO DYE; SOLVENT; SYNTHESIS; TEMPERATURE;

EID: 58249114866     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2008.10.011     Document Type: Article

References (20)

1. Zollinger H. Azo and diazo chemistry, aliphatic and aromatic compounds (1961), Interscience Publishers Ltd., London
2. Saunders K.H., and Allen R.L.M. Aromatic diazo compounds. 3rd ed. (1985), Edward Arnold (Publishers) Ltd., London
3. Clark J.H. Chemistry of waste minimization (1995), Chapman and Hall, London
4. Clark J.H. Catalysis of organic reactions by supported inorganic reagents (1994), VCH, New York
5. Okahara T. Water-tolerant solid acid catalysts. Chem Rev 102 (2002) 3641-3666
6. Dabbagh A.H., Teimouri A., and Najafi Chermahini A. Green and efficient diazotization and diazo coupling reactions on clays. Dyes Pigments 73 (2007) 239-244
7. Damodaran B., Litka J., and Malathy L. Modified clays as efficient acid-base catalyst systems for diazotization and diazo coupling reactions. Synth Commun 33 (2003) 863-869
8. Doyle M.P., Siegfried B., and Dellaria Jr. J.F. Alkyl nitrite-metal halide deamination reactions. 2. Substitutive deamination of arylamines by alkyl nitrites and copper (II) halides. A direct and remarkably efficient conversion of arylamines to aryl halides. J Org Chem 42 (1977) 2426-2430
9. 2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions. Tetrahedron 57 (2001) 9509-9511
10. 2 as a novel heterogeneous system for the oxidation of 1,4-dihydropyridines under mild conditions. Green Chem 4 (2002) 562-564
11. Hajipour A.R., Mirjalili B.B.F., Zarei A., Khazdooz L., and Ruoho A.E. A novel method for sulfonation of aromatic rings with silica sulfuric acid. Tetrahedron Lett 45 (2004) 6607-6609
12. Zolfigol M.A., Mirjalili B.B.F., Bamoniri A., Karimi M.A., Zarei A., Khazdooz L., et al. Nitration of aromatic compounds on silica sulfuric acid. Bull Korean Chem Soc 25 (2004) 1414-1416
13. Hajipour A.R., Zarei A., Khazdooz L., Mirjalili B.B.F., Sheikhan N., Zahmatkesh S., et al. Silica sulfuric acid as an efficient heterogeneous catalyst for the synthesis of 1,1-diacetates under solvent-free conditions. Synthesis 20 (2005) 3644-3648
14. Hajipour A.R., Zarei A., and Ruoho A.E. Efficient method for iodination of alcohols using KI/silica sulfuric acid (SSA). Synth Commun 36 (2006) 1039-1050
15. Dictionary of organic compounds. 5th ed. (1982), Chapman and Hall
16. Carey F.A., and Sundberg R.J. Advance organic chemistry, Part B: reaction and synthesis. 3rd ed. (1993), Plenum Press, New York p. 589
17. Akelah A., and Moet A. Functionalized polymers and their applications (1990), Chapmam and Hall
18. Hodge P., and Sherrington D.C. Polymer-supported reactions in organic synthesis (1992), John Wiley & Sons
19. Toda F., and Tanaka K. Solvent-free organic synthesis. Chem Rev 100 (2000) 1025-1074
20. Tanaka K. Solvent-free organic synthesis (2003), Wiley-VCH GmbH & Co. KGaA