Abstract
Synthesis of alkyl/aryl [2-(1,2,4,5-tetrahydro-3-sulfanylene/selenylene naphtha[1,8-f,g][1,5,3]diazaphosphocin-3-yl) methyl amino acid esters] (6, 7, 8, 9, 10, 11, 12, 13, 14, 15) was accomplished in three steps. 1, 8-diamino naphthalene (2) was reacted with tris (bromomethyl) phosphine (1) in the presence of triethylamine in dry tetrahydrofuran (THF) under N2 atmosphere to form a PIII intermediate (3). It was converted to the corresponding sulfide (4) and selenide (5) by reacting with sulfur and selenium, respectively. The intermediates 4 and 5 were further reacted with amino acid esters to obtain the title compounds (6, 7, 8, 9, 10, 11, 12, 13, 14, 15). The structures of the title compounds were established by elemental analysis and spectral data (IR, 1H, 13C, 31P NMR, and FAB mass). The antimicrobial activity of these compounds was evaluated and they exhibited significant activity. J. Heterocyclic Chem., (2010).
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