19585-93-4Relevant academic research and scientific papers
13C and 1H NMR Studies of Structure and Tautomerism in Some Perimidines
Woodgate, P. D.,Herbert, J. M.,Denny, W. A.
, p. 191 - 196 (1988)
The 13C NMR spectra of some 1- and 2-substituted perimidines and perimidinium salts are discussed and assigned.Although the spectra of most of the 2-substituted perimidines are comparatively simple, several examples display 13C and 1H spectral characteristics indicative of inhibition of prototropic tautomerism.KEY WORDS 13C NMR Perimidines Perimidinium salts 1H NMR Tautomerism
HETEROCYCLIC ANALOGS OF PLEIADIENE. 61. 2-CYANO- AND 2-CARBAMOYLPERIMIDINES
Suslov, A. N.,Pozharskii, A. F.,Borovlev, I. V.
, p. 691 - 693 (1993)
Treatment of 1-R-2 chloroperimidines with potassium or sodium cyanides in DMSO solution leads to facile substitution of the chlorine atom by the CN group and formation of previously unknown 1-R-2-cyanoperimidines.The latter upon heating in polyphosphoric acid are converted to 1-R-2-carbamoylperimidines in good yield.
Potential Antitumor Agents. 53. Synthesis, DNA Binding Properties, and Biological Activity of Perimidines Designed as "Minimal" DNA-Intercalating Agents
Herbert, John M.,Woodgate, Paul D.,Denny, William A.
, p. 2081 - 2086 (1987)
A series of compounds based on perimidine have been synthesized and evaluated for their DNA-binding properties and antitumor activity.The fused tricyclic perimidine chromophore appears to be the minimal structural requirement for intercalative binding to DNA since the mode of binding could be dictated by the position of attachment of the side chain.The intercalating compounds have DNA association constants (log K = 5.8-6.5) and cytotoxic potencies (IC50 = 500-1500 nM) comparable to those shown by other classes of linear, tricyclic DNA-intercalating antitumor agents (acridinecarboxamides, phenazinecarboxamides), but none of the compounds showed in vivo activity.
Carboxylate ligand-induced intramolecular C-H bond activation of iridium complexes with N -phenylperimidine-based carbene ligands
Tsurugi, Hayato,Fujita, Shingo,Choi, Gyeongshin,Yamagata, Tsuneaki,Ito, Syoji,Miyasaka, Hiroshi,Mashima, Kazushi
experimental part, p. 4120 - 4129 (2010/12/19)
We report the synthesis and structure of iridium(I) complexes with N,N′-disubstituted perimidine carbene ligands and halides or carboxylate ligands. Iodo-, chloro-, and acetate-Ir(carbene)(cod) complexes were selectively prepared by changing the bases and silver salts. Intramolecular C-H bond activation to prepare a cyclometalated Ir(III) complex, (C-C:) 2Ir(OAc) (6), where C-C: is a cyclometalated perimidine carbene ligand, was achieved using a carboxylate-ligated iridium complex; otherwise, C-H activation did not proceed. Acetate-Ir(carbene)(cod) (3c) reacted with benzoic anhydride at room temperature to afford benzoate-Ir(carbene)(cod) (3d). A perimidine-carbene- and phenylpyridine-ligated Ir(III) complex, (C -C:)(C-N)Ir(OCOR) (8), where C-N is a cyclometalated phenylpyridine ligand, was isolated in good yield by mixing 3c or 3d and phenylpyridine under reflux in toluene. On the basis of the formation of 1,3-cyclooctadiene from the reaction mixture, we propose the following reaction mechanism for the intramolecular C-H activation: carboxylate-induced C-H bond activation and subsequent pyridine- or carbene-directed C-H bond oxidative addition, followed by the isomerization of 1,5-cyclooctadiene and reaction with carboxylic acid produces (C-C:)(N-C:)Ir(OCOPh). The cyclometalated complex 6 reacts with sodium acetylacetonate to form (C -C:)2Ir(acac) (11), which exhibits phosphorescent emission at max = 555 nm (τ = 0.65 μs, φPL = 0.0018) in CH2Cl2 solution at room temperature.
HETEROCYCLIC ANALOGS OF PLEIADIENE. LVI. A NEW REACTION OF PERIMIDINES AND BENZIMIDAZOLES - DIMERIZATION UNDER THE INFLUENCE OF DILITHIOBENZOPHENONE WITH SUBSEQUENT AROMATIZATION OF ONE HETEROCYCLE AND OPENING OF THE OTHER
Pozharskii, A. F.,Smirnova, L. P.,Klyuev, N. A.,Starshikov, N. M.
, p. 1427 - 1434 (2007/10/02)
Under the influence of dilithiobenzophenone in THF 1-substituted perimidines and benzimidazoles undergo dimerization at position 2.The initially formed dilithio derivative of the bisdihydro compound then undergoes a complex transformation of the hydride disproportionation type, as a result of which one of the heterocycles on the dimer is aromatized while the other is opened.
PERI-NAPHTHYLENE DIAMINES III. CONVENIENT METHOD FOR THE ALKYLATION OF 1,8-NAPHTHYLENEDIAMINES AND PERIMIDINES
Kurasov, L. A.,Posharskii, A. F.,Kuz'menko, V. V.
, p. 1735 - 1738 (2007/10/02)
In dimethyl sulfoxide or hexamethylphosphorotriamide in the presence of potassium hydroxide 1,8-naphthylenediamine is readily alkylated by an excess of methyl and ethyl iodide to the corresponding 1,8-bis(dialkylamino)naphthalene.Perimidone, which has low basicity, is methylated to 1,3-dimethylperimidone under these conditions.The potassium hydroxide-dimethyl sulfoxide system also secures higher yields of the N-substituted products during the alkylation of perimidine, 2-methylperimidine, and aceperimidine by alkyl halides compared with the potassium hydroxide-alcoholsystem.The yield and structure of the products from benzylation of the perimidines depend on the presence of substituents at position 2 of the heterocyclic system of perimidine.
PERI-NAPHTHALENEDIAMINES. II. GENERAL METHOD FOR THE SYNTHESIS OF TETRA-, TRI-, AND DI-N-SUBSTITUTED 1,8-NAPHTHYLENEDIAMINES
Pozharskii, A. F.,Kurasov, L. A.,Kuz'menko, V. V.,Popova L. L.
, p. 884 - 891 (2007/10/02)
By the action of alkalis or lithium aluminum hydride 1,1,3-trialkyl- and 1,1-dialkyl-3-acetyl-2,3-dihydroperimidinium salts are converted smoothly into di-, tri-, or tetraalkyl-substituted 1,8-naphthylenediamines.If the number of N-ethyl groups in the 1,8-naphtylenediamines is increased, their basicity and the strength of the intramolecular hydrogen bond increases.
Heterocyclic Analogs of Pleiadiene. 51. N-Acylperimidines: Ring Opening Instead of Deacylation under the Influence of Nucleophiles
Pozharskii, A. F.,Dal'nikovskaya, V. V.,Pozharskaya, S. S.,Sheinkman, A. K.
, p. 1064 - 1068 (2007/10/02)
N-Acetyl- and N-benzoylperimidines, as well as quaternary salts based on them, were synthesized.It is shown that the heteroring is opened to give N-acyl derivatives of 1,8-naphthalenediamine by the action of nucleophiles on N-acylperimidines and N-benzoylperimidine salts.
HETEROCYCLIC ANALOGS OF PLEIADIENE. 48. PYROSULFITE AS A MILD DEHYDROGENATING AGENT IN THE 2,3-DIHYDROPERIMIDINE SERIES. SYNTHESIS OF 2-POLYHYDROXYALKYLPERIMIDINES
Starshikov, N.M.,Pozharskii, A.F.
, p. 81 - 85 (2007/10/02)
2,3-Dihydroperimidines are dehydrogenated smoothly by sodium pyrosulfite in refluxing aqueous alcohol, as a result of which the corresponding perimidines are formed in high yields.The reaction of 1,8-naphthalenediamine with the aldehydic forms of sugars gives 2-polyhydroxyalkyl-2,3-dihydroperimidines, which are also aromatized by sodium pyrosulfite to give the corresponding 2-polyhydroxyalkylperimidines in high yields.
