Synthesis of calix[4]aren derivative containing flavin group

The study comprises synthesis of 25,27-bis-3-cyanopropoxicalix[4]arene (3) and N1-Chloroacetyl-N3-methylisoalloxazine (7) and treatment of these two compounds under suitable conditions.Structures of these compounds were characterized by spectroscopic techniques (FTIR, 1H NMR) and elemental analysis.Synthetic work was carried out according to the methods described in the literature. After the synthesis of 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra-hydroxycalix[4]-arene 1, a solution of this compound in toluene was treated with phenol in the presence of AlCl3 to obtain calix[4]arene (2). 25,27-bis-3-cyanopropoxicalix[4]arene (3) obtained by treatment of this compound with 4-chlorobutylnitrile in dry acetonitrile in the presence of K2CO3 and NaI. In another work, N1-chloroacethyl-N3-methylisoalloxazine (7) was synthesized. On the purpose of to synthesise of compound (7), first of all nitro groups of 1,2-dinitrobenzen were reduced to amino groups by the treatment of this compound in acetic acid with Pd (%10 C) under H2 gas. Then it was treated with 3-methylalloxan in the presence of H3BO3 to obtain N3-Methylisoalloxazine (4). Secondly Ethyl-N3-methylisoalloxazine-1-acetate (5) was obtained by the treatment of this compound (5) with ethylbromoacetate in DMF in the presence of K2CO3. Ester group of this compound (5) was hydrolysed to acid derivative (6) by the treatment of this compound with HCl. Then N1-chloroacethyl-N3-methylisoalloxazine (7) was synthesized by the treatment of compound 6 with SOCl2. Finally compound 7 was treated with compound 3 in CH3CN in the presence of K2CO3 to obtain compound (8).2008, Page: 67Keywords: calix[4]arene, calixflavin, isoalloxazine