BF3.SiO2: an efficient catalyst for the synthesis of azo dyes at room temperature


Bi Bi Fatemeh Mirjalilia, Abdolhamid Bamoniri and Ali Akbari


A rapid one-pot method has been developed for the synthesis of azo dyes via ‎sequential diazotization–diazo coupling of aromatic amines with coupling agents at room ‎temperature in the presence of BF3.SiO2 as acidic catalyst. The obtained aryl diazonium salts bearing silica supported boron tri-flouride counter ion‎ was sufficiently stable to be kept at room ‎temperature in the dry state.‎


DOI: j.ccl.2012.6.002

Keywords: Azo dye ,BF3.SiO2 ,Stable diazonium salts Diazotization ,Lewis acid

How to cite this paper:

Mirjalilia, B., Bamoniri, A & Akbari, A. (2012). BF3.SiO2: an efficient catalyst for the synthesis of azo dyes at room temperature.Current Chemistry Letters, 1(3), 109-114.


References

‎Karci, F.; Demircali, A.; Sener, I.; Tilki, T. (2006) Synthesis of 4-amino-1H-‎benzo[4,5]imidazo[1,2-a]pyrimidin-2-one and its disperse azo dyes. Part 1: Phenylazo ‎derivatives, Dyes and Pigments 71, 90-96.‎

Sharma, P.; Rane, N.; Gurram, V. K. (2004) Synthesis and QSAR studies of ‎pyrimido[4,5-d]pyrimidine- 2, 5-dione derivatives as potential antimicrobial agents, ‎Bioorg. Med. Chem. Lett. 14, 4185–4190.

‎Sadegi, B.; Mirjalili, B. F.; Hashemi, M. M. (2008) BF3.SiO2: An efficient reagent ‎system for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles, Tetrahedron ‎Lett. 49, 2575-2577.

‎Mirjalili, B.F.; Bamoniri, A.; Akbari, A. (2008) BF3.SiO2: An efficient alternative for ‎the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes, Tetrahedron Lett. 49, ‎‎6454-6456.‎

Mirjalili, B. F.; Bamoniri, A.; Akbari, A. (2011) Nano-BF3.SiO2: a reusable and eco-‎friendly catalyst for synthesis of quinoxalines, Chem. Heterocycl. Comp., 47, 487-491.‎

‎Mirjalili, B. F.; Bamoniri, A.; Akbari, A. (2011) One-Pot Synthesis of 3,4-‎Dihydropyrimidin-2(1H)-ones (Thiones) Promoted by Nano-BF3.SiO2, J. Iran. Chem. ‎Soc., 8, S135-S140.

‎‎Mirjalili, B. F.; Bamoniri, A.; Akbari, A. (2011) Nano-BF3.SiO2: Areusable and eco-‎friendly catalyst for thioacetalization and trans-thioacetalization reactions, Iranian J. ‎Catal. 1, 87-92.

‎Pourjavadi, A., Mirjalili, B. F., Entezami, A. A.; Zohuriaan-Mehr, M. J. (2001), Novel ‎azo containig polymethacrylates bearing spiroacetalmoeity and methylene spacers: ‎synthesis and characterization, Eur. Poly. J. 37, 2111-2121.‎