Decahydroacridine-1,8-dione

PEGs were found to be the most efficient solvent for e CAN-catalyzed synthesis of N-aryl-decahydroacridine-1,8-diones 123 (Scheme 71) [102]. In the screening for a suitable solvent, PEG 200, PEG 400, and PEG 600 demonstrated identical results. No decrease in the product yield was observed after three runs of the reaction using recovered PEG 400. 

The enaminone 239, prepared from dimedone and ammonia, is converted into the spiro compound 240 by the action of formaldehyde in dilute hydrochloric acid, but under neutral conditions the di(enaminone) 241 is formed. The latter cyclizes under the influence of hydrochloric acid to a derivative 242 of decahydroacridine dione (equation 101)124... 

Decahydroacridine-l,8-dione 356 (R = R1 = H) was synthesized by firstly reacting dimedone with hexamine in aqueous methanol solution to give bzs(dimedonyl)methane. Subsequent treatment with concentrated ammonia and ammonium carbonate in autoclave gave 356 (95MI19)... 

M. Kidwai, D. Bhatnagar, Ceric ammonium nitrate (CAN) catalyzed synthesis of N-substituted decahydroacridine-l,8-diones in PEG, Tetrahedron Lett. 51 (2010) 2700-2703. 

A. Rajack, K. Yuvaraju, C. Praveen, Y.L.N. Murthy A facile syntheis of 3,4-dihydropyrimidinones/thiones and novel N-dihydro pyrimldinone-decahydroacridine-l,8-diones catalyzed by cellulose sulfuric acid, J. Mol. Catal. A Chem. 370 (2013) 197-204. 

Timpe, H.-J., Ulrich, S., and Fouassier, J.-P., Photochemistry and use of decahydroacridine-l,8-diones as photosensitizers for onium salt decomposition,/. Photochem. Photobiol., A Chem., 73,139,1993. 

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