Synthesis and structural study of novel selenation derivatives of N, N-Dialkylcyanamides

Abstract

The reaction of 2,4-bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide {[PhP(Se)(µ-Se)]2, Woollins’ reagent, WR } with N, N-dialkylcyanamides 1–3 in refluxing toluene solution led to the corresponding [2+3] cycloaddition products 4-dialkylamino-2,5-diphenyl-1,3,2,5-selenazadiphosphole 2,5-diselenides 4–6 in good yields, the latter were further treated with water resulting in the corresponding hydrolysis derivatives dialkyl-selenoureas 7–9 , and phosphinodiselenoates 10 and 11 . Selenourea 7 could be transferred into 1,3-selenazol-2-amines 12–15 in excellent yields by further cyclization with four different α-haloketones. All new compounds have been characterized by IR spectroscopy, multi-NMR (1H, 13C, 31P, 77Se) spectroscopy and accurate mass measurement. The single crystal X-ray structural features of nine new compounds are also discussed.