ChemInform Abstract: Reaction of Some 2‐Nitro‐2‐azapropanol Derivatives with Azoles.

Abstract

The reactions of the title compounds (I) and (VIII) using reaction conditions A) and B), resp., provides the various heterocyclic products shown in the scheme.

New Energetic Materials featuring Tetrazoles and Nitramines – Synthesis, Characterization and Properties

“…1-(2-Nitro-2-azapropyl)-5-aminotetrazole (8), 1-(2-nitro-2-azapropyl)-5H-tetrazole (9), 1-(2-nitro-2-azapropyl)-5-nitriminotetrazole (10·H 2 O, 10·EtOH), 2,5-bis(2-nitro-2-azapropyl)-5-nitraminotetrazole (11), 1-methyl-5-(2-nitro-2-azapropyl)-5-nitraminotetrazole (12), 1-methyl-4-(2-nitro-2-azapropyl)-5-nitriminotetrazole (13), 1-methyl-5-(2-nitro-2-azapropyl)-5-aminotetrazole (14) and 2-methyl-5-(2-nitro-2-azapropyl)-nitraminotetrazole (15) could be synthesized, mostly in good yields from deprotonated 5-amino-1H-tetrazole (3), 1H-tetrazole (4), 5-nitriminotetrazole (5), 1-methyl-5-nitriminotetrazole (6) and 2-methyl-5-nitramino-tetrazole (7), respectively.…”

“…The isomer 1-methyl-4-(2-nitro-2-azapropyl)-5-nitriminotetrazole (13) was obtained only in very low yields and was detected due to its different crystal shape, while crystal picking of 12. A third product (~12 %) 1-methyl-5-(2-nitro-2-azapropyl)-5-aminotetrazole (14) was obtained as colorless crystals by allowing the mother liquor to stand for a few days. The mechanism of the formation of 14 has not been clarified yet.…”

“…There are strong similarities between the NMR spectra of 12, 14, and 15, which only differ in the position of the methyl group (12 and 15) or concerning the nitro group at N5 (12 and 14). In all spectra, N3 is shifted downfield [9.9 ppm (12), 1.3 ppm (14), and 1.4 ppm (15) …”