U. Anasuyamma, P. Haranath, B. S. Kumar
2007
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Journal
Heterocyclic Communications
Abstract
Substituted dinaphtho-16H-(2,1 d ( l \2'-g)l ,3,2-dioxaphosphocin-8-yl]ureas (5a-i) were synthesized by reacting bis (2-hydroxy-l-naphthyl)methane (4) with different carbamidophosphoric acid dichlorides (3) in the presence of triethylamine in dry toluene at 45-50 °C. Their structures were established by elemental analysis, IR, H, C & P NMR spectral data. These compounds were found to possess good antimicrobial activity. Introduction Organophosphorus compounds being ubiquitous in nature have found multifaceted applications. Phosphorous heterocycles substituted with carbamate moieties are important classes of antitumour agents [1], pesticides [2], and bactericides [3, 4]. Substituted phosphoryl ureas of the type RR'P(0)NHC0NR" R'" exhibited pesticidal activity [5-7]. In view of this several, N(substituted)-JV-[8-oxidodinaphtho-l6H-(2,1 -d: (1 ',2'-g)l,3,2-dioxaphosphocin-8-yl]ureas have been synthesized, expecting them to possess broad spectrum of biological activity and characterized by elemental, IR, NMR (*Η, C and P) spectral analyses. Results and Discussion The synthetic route (Scheme-1) involves the addition of dichloroisocyanato phosphine oxide [1, 8] (1) with various amines (2a-i) at -15°C under inert anhydrous conditions in dry toluene to afford the corresponding carbamidophosphoric acid dichlorides [9, 10] (3a-i). After the completion of addition of amines to 1, the products separated from the reaction mixture immediately as crystalline compounds. Further purification of carbamidophosphoric acid dichlorides (3a-i) could not be accomplished due to their insolubility in many organic solvents and air sensitivity. Hence they were reacted directly in situ with a solution of bis (2-hydroxy-lnaphthyl)methane (4) in toluene in the presence of two equivalents of triethylamine to yield the compounds 5a-i and their structures were established by IR, NMR (*H, C and P) spectral data (Tables-1,2 and 3).