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Гусейнов, Ф. И.; Asadov, Kh. A.; Burangulova, R. N.; Москва, В. В.

doi:10.1023/a:1012720524979

Cited by 4 publications

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“…The conformation along the P-C (12) and C (8) -C (12) bonds is staggered, perhaps due to steric effects; steric hindrance is minimal in this conformation. The N (2) -C (3) -N (7) -C (8) torsion angle is 11.5(4)°, resulting from conjugation of the unshared electron pair of N (7) with the π-system of the furazane ring. The phenyl substituent at C (12) is in an eclipsed conformation with the C (12) -Cl bond, probably due to steric hindrance arising from the bulky substituents at C (12) .…”

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“…In previous work [3], we showed that diethoxyphosphorylphenyl-α-chloroacetaldehyde in a polar solvent (acetonitrile) reacts with diaminofurazane to give semiaminal 5a but this reaction in ethanol gives O,N-acetal 5b, whose structure was demonstrated by X-ray diffraction structural analysis. Since the crystal of 5b is centrosymmetric, this compound exists as a racemate (Fig.…”

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“…The P=O and C-Cl bonds in 5b are in gauche arrangement, while the C (8) -C (12) bond is trans to the phosphoryl bond. The C (3) -N (7) bond length (1.345(4) Å) corresponds to this conjugation. The aminofurazane substituent has planar conformation.…”

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“…2) between the aminofurazane group and phosphoryl group oxygen atom N (7) -H···O (21') (3/2-x, 1/2+y, 1/2-z), N (7) -H 0.93, N (7) ···O (21') 3.042 (3); H···O (21') 2.15 Å, angle N (7) -H···O (21') 161° and also between the amino NH 2 group, phosphoryl group, and one of the nitrogen atoms of the furazane ring: N (6) -H (61) ···O (21') , N (6) -H (61) 0.75, N (6) ···O (21') 2.903(4), H (61) ···O (21') 2.16 Å, angle N (6) -H (61) ···O (21') 173°; N (6) -H (62) ···N (5'') (2-x, 2-y, -z), N (6) -H (62) 1.12, N (6) ···N (5'') 3.019(4), H (62) ···N (5'') 1.94 Å, angle N (6) -H (62) ···N (5'') 161°. 2) between the aminofurazane group and phosphoryl group oxygen atom N (7) -H···O (21') (3/2-x, 1/2+y, 1/2-z), N (7) -H 0.93, N (7) ···O (21') 3.042 (3); H···O (21') 2.15 Å, angle N (7) -H···O (21') 161° and also between the amino NH 2 group, phosphoryl group, and one of the nitrogen atoms of the furazane ring: N (6) -H (61) ···O (21') , N (6) -H (61) 0.75, N (6) ···O (21') 2.903(4), H (61) ···O (21') 2.16 Å, angle N (6) -H (61) ···O (21') 173°; N (6) -H (62) ···N (5'') (2-x, 2-y, -z), N (6) -H (62) 1.12, N (6) ···N (5'') 3.019(4), H (62) ···N (5'') 1.94 Å, angle N (6) -H (62) ···N (5'') 161°.…”

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C-phosphorylated furazano-[3,4-b]piperazines

Asadov

Гусейнов

Strunin

et al. 2006

Chem Heterocycl Compd

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The reaction of phosphorylated α-chloroacetaldehydes with 3,4-diaminofurazane gives enamines, bisenamines, semiaminals, and O,N-acetals, whose cyclization leads to previously unreported phosphorylated furazano[3,4-b]piperazines.Derivatives of furazano [3,4-b]piperazines are used as energy-rich materials, intermediates in organic synthesis, and biologically active compounds. However, preparative methods for obtaining these compounds and the chemical properties of these derivatives, which may have potential as biologically active compounds, have not been studied adequately [1,2].With the aim of synthesizing C-phosphorylated furazanopiperazines, we studied the reactions of α-chloroacetaldehydes 1 with diaminofurazane. The condensation of phosphorylmonochloroacetaldehydes 1a,b with 3,4-diaminofurazane proceeds in ethanol at reflux and leads to the formation of monoenamine 2 and bisenamine 3 depending on the ratio of the starting reagents. + 2, 3 a R = Et, b R = i-Pr Enamines 2 and 3 are white crystalline compounds. The IR band for their amino group is found at 3350 cm -1 and is superimposed on the stretching band of the secondary amino group to give a complex overall shape. The low value for ν NH 2 in KBr pellets indicates hydrogen bonding of this group. __________________________________________________________________________________________

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C-phosphorylated furazano-[3,4-b]piperazines

Asadov

Гусейнов

Strunin

et al. 2006

Chem Heterocycl Compd

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ChemInform Abstract: 4‐Diethoxyphosphoryl‐5‐ethoxy‐4‐phenyl‐3,4,5,6‐tetrahydrodiazino [2,3‐c]furazane.

et al. 2002

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2002organo-phosphorus compounds organo-phosphorus compounds S 0080 4,5,furazane.-Reaction of diaminofurazane (I) with phosphorylacetaldehyde (II) in EtOH gives the hemiaminal (V), which cyclizes in the presence of EtONa to furnish the title compound (VI), the first phosphorylated diazino[2,3-c]furazane reported, in high yield.-(GUSEINOV, F. I.; ASADOV, KH. A.; BURANGULOVA, R. N.; MOSKVA, V. V.; Chem.

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