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Dense compounds of C, H, N, and O atoms: II [1]. Nitramine and nitrosamine derivatives of 2-oxo- and 2-iminooctahydroimidazo-[4,5-d]imidazole

✍ Scribed by Vayalakkavoor T. Ramakrishnan; Murugappa Vedachalam; Joseph H. Boyer

Book ID: 102235309
Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 428 KB
Volume: 2
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520020611

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✦ Synopsis

The 4,6-dinitroso derivative 11 was obtained (83%) by the nitrosation of 2-oxooctahydroimidazo [ 4,5-d]imidazole 1 as the dihydrochloride and was converted to the 4,6-dinitro derivative 12 [ 66%] by treatment with nitric acid (loo%, -40°C) and to the 1.4,6-trinitro derivative 13 (66%) and the I,3,4,6-tetranitro derivative 2 (86%) by treatment with nitric acid (1OWo) in acetic anhydride at 0-5°C and 10-25°C respectively. Similar treatment with nitric acid (100%) i n either acetic or trifluoroacetic anhydride at 0-25°C converted the trinitro compound 13 to the tetranitro compound 2 (86%). The dinitramine 12 was also obtained (43%) from the diarnine 1 by nitration with nitric acid (100%' -40°C). A reaction between 2-nitrimino-5-iminooctahydroimidazo [ 4,5-d]imidazole 7 as a hydrochloride salt (from a n acid catalyzed condensation between 4,5-dihydroxy-2-nitriminoimidazolidine 6 and guanidine) and nitric acid (loo%, -40°C) gave the 2,5-dinitrimino derivative 14 (85%) isolated as a monohydrate. The nitrate salt 7 . HN03, isomeric with 14 . HzO, was obtained from the corresponding hydrochloride 7 -HCl and silver nitrate.

Both nitrimines 7 and 14 gave I ,3,4,6-tetranitro-2,5dioxooctahydroimidazo[ 4,5-d]irnidazole 15 (66% and 59%) by treatment with nitric acid (100%) in acetic anhydride.

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