III International Conference

PP-I-27In our previous research we have studied influence of reaction conditions on a proceedingof reductive debenzylation-acylation of HAIW (R=H), yield of a key intermediate (TADFIW)and stability of palladium-based catalyst [4]. In the further works the correlations between"structure-activity" and "structure-stability" are investigated for various types of Pd/Ccatalysts [5]. However despite of the certain improvements the stability of the best palladiumcatalyst was not increased significantly.ArH 2 CNCH 2 ArN CH 2 ArNNAr =RIn the present work we have studied the one-potreductive dearylation-acylation of substitutedhexaarylhexaazaisowurtzitanes over palladium-NArH 2 CN CH 2 ArCH 2 Ar3, HAIWbased catalysts. Several benzylamines have beensuccessfully condensed with glyoxal to producesubstituted HAIW e.g. hexa(4-methoxybenzyl)hexaazaisowurtzitane (R=OCH 3 ) [6]. Thegeneral kinetic peculiarities of reaction are investigated. Also stability of the Pd/C catalyst inthe dearylation process was studied. The opportunity of nitramines precursors synthesiswithout use of formic acid is checked up (dearylation of six aryl groups in one step). Dataobtained can serve as a basis for the further development of a highly effective method ofHNIW synthesis.Reference1. Nielsen A.T., Chafin A.P., Christian S.L., Moore D.W., Nadler M.P., Nissan R.A.,Vanderah D.J., Gilardi R.D., George C.F., Flippen-Andersen J. Tetrahedron. 54, 11793 (1998)2. Наир У.Р., Сиваблан Р., Гор Г.М., Гиза М., Астина Ш.Н., Сингх Х. Физика горения ивзрыва. 3, 3 (2005)3. Wardle R.B., Edwards W.W. Пат. 5723604 США; Chem. Abstr., 135, 332979 (2001)4. Koskin A.P., Simakova I.L. Perspectives of making and application of the condensed energeticmaterials (Texts of reports of the 1 st Russian scientific and technical conference, in russian),Biisk, 2006. p.425. Koskin A.P., Simakova I.L. Perspectives of making and application of the condensed energeticmaterials (Texts of reports of the 1 st Russian scientific and technical conference, in russian),Biisk, 2006. p.476. M.R.Crampton, J.Hamid, R.Millar, G.Fergusson. J. Chem. Soc., Perkin Trans. 2, 923 (1993)57