Abstract
6-Acetyl-7-methylpteridine derivatives 2 and 3 (lumazine and pterin) were converted to 6-[1-(arylamino)ethyl]pteridine derivatives 8 and 7, respectively, in good to moderate yields by stepwise reactions with p-substituted anilines via imine intermediates using a Lewis acid catalyst followed by treatment with sodium tetrahydroborate. The one-step reductive amination of the starting acetylpteridine also proceeded in the presence of 2-picoline-borane complex in satisfactory yield.
References
Goldberg, D. E. When the host is smarter than the parasite. Science 2002, 296, 482–483.10.1126/science.1071206Search in Google Scholar PubMed
Jones, W. J.; Nagel, D. P. Jr.; Whitman, W. B. Methanogens and the diversity of archaebacteria. Microbiol. Mol. Biol. Rev. 1987, 51, 135–177.10.1128/mr.51.1.135-177.1987Search in Google Scholar PubMed PubMed Central
Murata, S.; Ichinose, H.; Urano, F. Tetrahydrobiopterin and related biologically important pterins. In Topics in Heterocyclic Chemistry Vol. 8. Bioactive Heterocycles II; Eguchi, S., Ed. Springer: Berlin, 2007, pp. 127–171.10.1007/7081_2007_061Search in Google Scholar
Pfleiderer, W.; Gerhard, H. Pteridines – part CXVIII – methanopterin, chemical approach and partial synthesis. Helv. Chim. Acta 2007, 90, 1856–1873.10.1002/hlca.200790195Search in Google Scholar
Sato, S.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. One-pot reductive amination of aldehydes and ketones with α-picoline-boran in methanol, in water, and in neat conditions. Tetrahedron 2004, 60, 7899–7906.10.1016/j.tet.2004.06.045Search in Google Scholar
Shiro, Y.; Urano, F.; Kuroda, Y.; Murata, S. A convenient synthesis of optically active biopterin. Heterocycles 2008, 76, 1329–1335.10.3987/COM-08-S(N)99Search in Google Scholar
Tada, M.; Wada, M. Synthesis of 1-allyl-6-(arylamino)methyl-7-methyl-3-phenylpteridine-2,4-dione, a methanopterin analogue. J. Chem. Res. Synopsis 2003, 648–649.10.3184/030823403322655950Search in Google Scholar
White, R. H. Biosynthesis of methanopterin. Biochemistry 1996, 35, 3447–3456.10.1021/bi952308mSearch in Google Scholar PubMed
Zhang, K.; Rathod, P. K. Divergent regulation of dihydrofolate reductase between malaria parasite and human host. Science 2002, 296, 545–547.10.1126/science.1068274Search in Google Scholar PubMed PubMed Central
©2012 Walter de Gruyter GmbH & Co. KG, Berlin/Boston
Articles in the same Issue
- Supplementary data
- Masthead
- Masthead
- Preliminary Communications
- Synthesis and molecular structure of (Z)-1H-purin-6-ylideneaminooxysulfonic acid: a possible secondary metabolite of adenine
- Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids
- Research Articles
- Reductive amination of 6-acetylpteridine to 6-N-arylaminoethylpteridine
- Efficient synthesis of selected phthalazine derivatives
- Synthesis of novel fluorescent 1,3,5-trisubstituted triazine derivatives and photophysical property evaluation of fluorophores and their BSA conjugates
- Fast and efficient microwave synthetic methods for some new 2(1H)-pyridone arabinosides
- Simple and efficient synthesis of novel N-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazines
- Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide
- Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction
- One-pot synthesis of acenaphtho[1,2-b]pyrroles in the presence of supported ionic liquid catalyst
- Theoretical investigation on tautomerism and NBO analysis of 3-hydroxy-1,2,5-thiadiazole derivatives: solvent and substituent effects
Articles in the same Issue
- Supplementary data
- Masthead
- Masthead
- Preliminary Communications
- Synthesis and molecular structure of (Z)-1H-purin-6-ylideneaminooxysulfonic acid: a possible secondary metabolite of adenine
- Design and synthesis of heterocyclic enamine derivatives based on skeleton of neonicotinoids
- Research Articles
- Reductive amination of 6-acetylpteridine to 6-N-arylaminoethylpteridine
- Efficient synthesis of selected phthalazine derivatives
- Synthesis of novel fluorescent 1,3,5-trisubstituted triazine derivatives and photophysical property evaluation of fluorophores and their BSA conjugates
- Fast and efficient microwave synthetic methods for some new 2(1H)-pyridone arabinosides
- Simple and efficient synthesis of novel N-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazines
- Palladium-catalyzed cascade reactions of benzyl halides with N,N-diallyl-p-toluenesulfonamide
- Iodine-catalyzed synthesis of 5-arylanthra[2,1-c][2,7]naphthyridine derivatives via three-component reaction
- One-pot synthesis of acenaphtho[1,2-b]pyrroles in the presence of supported ionic liquid catalyst
- Theoretical investigation on tautomerism and NBO analysis of 3-hydroxy-1,2,5-thiadiazole derivatives: solvent and substituent effects