111-53-5Relevant academic research and scientific papers
Facile and selective polynitrations at the 4-pyrazolyl dual backbone: Straightforward access to a series of high-density energetic materials
Domasevitch, Kostiantyn V.,Gospodinov, Ivan,Krautscheid, Harald,Klap?tke, Thomas M.,Stierstorfer, J?rg
, p. 1305 - 1312 (2019)
Nitro-functionalized energetic materials are still needed to meet new safety, performance and chemical accessibility demands. The problem of multiple C-nitrations on N-containing heterocycles was resolved successfully for the 4,4′-bipyrazole scaffold. A progression of gradually functionalized 3-nitro-4,4′-bipyrazole (2), 3,3′-dinitro-4,4′-bipyrazole (3), 3,5-dinitro-4,4′-bipyrazole (4), 3,3′,5-trinitro-4,4′-bipyrazole (5) and 3,3′,5,5′-tetranitro-4,4′-bipyrazole (6) was obtained in excellent yields by highly selective direct nitrations of 4,4′-bipyrazole (1). All synthesized polynitro derivatives 3-6 exhibit high decomposition temperatures of above 290 °C. The introduction of three (5) and four nitro groups (6) into the 4,4′-bipyrazole scaffold yields insensitive and thermally stable high explosives with excellent densities and detonation properties. The anhydrous structures of compounds 2-6 were obtained by low-temperature XRD. In addition, the performance of compounds 5 and 6 was investigated with a small scale shock reactivity test.
A New Synthetic Approach towards Adriamycin
Barton, Derek H. R.,Dawes, Clive C.,Franceschi, Giovanni,Foglio, Maurizio,Ley, Steven V.,et al.
, p. 643 - 647 (2007/10/02)
An improved route to 3,4-dihydro-2-phenylnaphthofuran-5-one (2) and a convenient preparation of furan-3,4-dicarbaldehyde (4) are described.The dihydro-derivative of (2) was condensed with (4) to give 4-(4-formyl-3-furylmethyl)-2-phenylnaphthofuran-5-one (5), which after preparation of its 1,3-dithiolan derivative was photocyclized to a polycyclic compound (7).Owing to problems of deprotection of (7) further steps towards adriamycin (1) were abandoned.
