Synthesis of 1-(N-nitropyrazolyl)-1Н-tetrazoles – a new type of heteronuclear N-nitropyrazole derivatives

Abstract

A general method has been developed for the synthesis of 1-pyrazolyl-1Н-tetrazoles, and N-nitration of these compounds was studied. The structural features affecting the direction of nitration were identified. A series of 1-(N-nitropyrazolyl)-1Н-tetrazoles was obtained, representing a new type of heteronuclear N-nitropyrazole derivatives.

Pyrazole–Tetrazole Hybrid with Trinitromethyl, Fluorodinitromethyl, or (Difluoroamino)dinitromethyl Groups: High‐Performance Energetic Materials

“…This compound was prepared by nitrating propanone 8 in a manner similar to that described above. Colorless solid; yield: 57 %; T dec 132 °C; IR (KBr): =3158, 3127, 2878, 1630, 1604, 1566, 1545, 1472, 1452, 1398, 1359, 1328, 1279, 1180, 1090, 1002, 983, 952, 889, 846, 814, 798 cm −1 ; 1 H NMR ([D 6 ]acetone): δ =8.74 (s, 1 H), 10.00 (s, 1 H); 13 C NMR ([D 6 ]acetone): δ =106.7 (C4), 120.2 (br s, C(NO 2 ) 3 ), 142.2 (C tetrazol ), 147.5 (C3), 147.7 ppm (C5‐NO 2 ); 14 N NMR ([D 6 ]acetone): δ =−35.1 (C5‐NO 2 ), −39.9 ppm (C(NO 2 ) 3 ); HRMS‐ESI: m / z calcd for [C 5 H 2 N 10 O 8 −NO 2 ] − : 284.0123; found: 284.0109; elemental analysis calcd (%) for C 5 H 2 N 10 O 8 (330.13): C 18.19, H 0.61, N 42.43; found: C 18.21, H 0.54, N 42.28.…”

“…[7] The 1-[1H-pyrazol-3(5)-yl]-1H-tetrazole biring system 1 [8] was identified as an attractive precursor for the development of new high-density, oxygen-rich energetic materi-als. [7] The 1-[1H-pyrazol-3(5)-yl]-1H-tetrazole biring system 1 [8] was identified as an attractive precursor for the development of new high-density, oxygen-rich energetic materi-als.…”

“…The design, synthesis, and characterization of new energetic ensembles of linearly bonded azoles with high density and reduced carbon content have been the focus of recent studies in our group . The 1‐[1 H ‐pyrazol‐3(5)‐yl]‐1 H ‐tetrazole biring system 1 was identified as an attractive precursor for the development of new high‐density, oxygen‐rich energetic materials. Based on computed predictions, the nitro‐, C(NO 2 ) 3 ‐, C(NO 2 ) 2 F‐, and C(NO 2 ) 2 NF 2 ‐substituted derivatives were envisaged as attractive synthetic targets.…”