Syntheses based on 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid hydrazide and azide

Treatment of 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid hydrazide with NH₄SCN and PhCONCS gave the corresponding thiosemicarbazides, arylsulfochlorides yielded the arylsulfonylhydrazides, and diazotization conditions gave the corresponding azide. The interactions of the latter with different nucleophiles have been studied and a series of novel carbamic acid, urea, and semicarbazide derivatives containing a thiazoline fragment have been prepared. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 430–436, March, 2006.     

水杨酰肼Schiff碱的合成、表征及抑菌活性

Sehiff碱具有多个氧、氮配位原子,是一类重要的生物配体,某些Schiff碱具有抗癌、抗病毒、抑制细菌生长等生物活性。本文制备了两个水杨酰肼类Schiff碱化合物,并探讨了结构组成、波谱性能及抑菌活性。     

Synthesis of n-vinyloxyethylated amides and ureas

Conclusions N-Vinyloxyethylated amides were synthesized by reacting the vinyl ethers of amino and ketimino alcohols with the acid chlorides of the 2,4-dichlorophenoxyacetic, o-, and p- chlorobenzoic acids, while the previously unknown N-vinyloxyethylated derivatives of ureas were obtained from the vinyl ethers of amino alcohols and aryl isocyanates.Translated fron Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1893–1896, August, 1981.     

Synthesis and properties of phenylogous amides

Vinylogy is a widely accepted principle involving the transfer of electronic chemical character through a double bond, and many reactions have been developed by applying this concept. In contrast, phenylogy, which involves the connection of two substituents through a benzene ring, is rarely recognized as a related idea. In this article, we present synthesis and physical properties, including their structure and reactivity of phenylogous amides. This amide mimetic unit is relatively stable and easily prepared by the Hartwig–Buchwald amination reaction. The effect of the resonance was examined by means of crystallography, reactivity and UV–vis spectroscopy.     

Synthesis and structures of new helical, nanoscale ferrocenylphenyl amides

Two novel ferrocenylphenyl-containing amides have been synthesized by reaction of ferrocenylbencarboxylchloride and 1, 2-di-(o_aminophenoxy)ethane. A single crystal X-ray analysis shows that compound 3 crystallizes in the triclinic system, space group P-1, and compound 4 crystallizes in orthorhombic system, space group Pca2₁. There are intramolecular H-bonds in both the compounds, two H-bonds in compound 3 and one in compound 4. The dihedral angels of Cp-ring and phenyl ring range from 3.8° to 20.8°. Translated from Chemical Research and Application, 2006, 18(2) (in Chinese)     

Synthesis,spectroscopic and structural perspective of new ferrocenyl amides

Two new ferrocene derivatives with amide linkages were synthesized by the condensation of 4-ferrocenylaniline with n-alkyl acid chloride derivatives as pristine orange solids in good yields. FTIR and ¹H/¹³C NMR studies have confirmed the basic structure of the molecules with the involvement of intermolecular H-bonding, which together with the ferrocene-like packing ensures the stability of the crystal structure. Crystal structures for both compounds were solved by Rietveld refinements of high resolution X-ray powder diffraction data. The XRD results show that both compounds crystallize in the monoclinic space group P2₁/c. The primary feature of the crystal structure is a double layer of ferrocenyl groups stretched out in the b-c -plane perpendicular to the a-axis, with packing of the ferrocenyl groups occurring in a manner similar to that of pure ferrocene. Despite the close structural similarity, both compounds differ in the optimized geometry of respective Ferrocene conformers. The Cp rings are eclipsed for one Ferrocene conformer and close to staggered for the other, owing to the low energy barrier for the rotation of a cyclopentadienyl ring relative to the rest of the molecule.     

Synthesis of nitroxylcarbamidophosphoric acid amides

A method for obtaining new organophosphorus nitroxyls was developed based on Kirsanov's phosphazo reaction.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1139–1141, May, 1990.     

Synthesis and disruption of a tetrametallic zinc hydrazide

Treatment of 1,1'-dimethylhydrazine, Me2NNH2 with excess diethylzinc affords a novel tetrametallic Zn4N8 cage complex, which on further reaction with tBuLi forms a lithium-bridged chain of Zn4N7 cages.     

Ab initio study of energetic solids: cupric azide, mercuric azide, and lead azide

We presented a detailed study on the electronic structure and optical properties of cupric azide (Cu(N(3))(2)), mercuric azide (alpha-Hg(N(3))(2)), and lead azide (alpha-Pb(N(3))(2)) by using density functional theory within the generalized gradient approximation. Relaxed crystal structures compare well with experimental data. An analysis of electronic structure, charge transfer, and bond order shows that Cu(N(3))(2) and alpha-Hg(N(3))(2) are covalent-type solids, whereas alpha-Pb(N(3))(2) is an ionic-type solid but has weak covalent character. The valence bands of Cu(N(3))(2) and alpha-Hg(N(3))(2) arise from the contributions of the metal-d and N-p states, whereas that of alpha-Pb(N(3))(2) are strongly dominated by N-p states and not from Pb-d states. The general shapes of the real and imaginary parts of the dielectric function, adsorption coefficient, and photoconductivity spectra for the three azides are similar. Our calculated optical properties are found to be in agreement with available experimental data. The absorption spectra show a number of absorption peaks in the fundamental absorption region. All the photoconductivity spectra display a broad photocurrent response in the fundamental absorption region. The density of states of the three azides reveal the effects of the metal states on the valence electron of the azide group and so are correlated with their impact sensitivity.     

Synthesis of thiophosphoric acid amides

Conclusions The cyclohexylamido- and piperididothiophosphoric acids were obtained for the first time, and also piperazido-N,N-bisthiophosphoric acid as the Na and NH₄ salts.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2402–2403, October, 1982.     

Synthesis of betulonic acid amides

Betulonic acid amides of interest as potential biologically active compounds were prepared. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 259–264, May–June, 2008.     

Lactams of acetals and acid amides, 45. Synthesis of condensed 2-pyridones from activated amides,lactams, and lactones

By reaction of lactim ethers with N-substituted cyanoacetamides, the corresponding enaminoamides were obtained, cyclization of which by dimethylformamide acetal gave derivatives of pyrrolo[3,2-c]pyridine, 1,6-naphthyridine, and pyrido[4,3-b]azepine, having a substituent at the nitrogen atom of the pyridone ring. N-substituted furo[3,2-c]pyridines were synthesized from the diethyl acetals of butyrolactone and 3-(dimethylaminomethylene)butyrolactone and dimethylformamide acetal.For communication 44, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 929–932, July, 1985.     

Synthesis of zirconium, hafnium, and tantalum complexes with sterically demanding hydrazide ligands

The bulky hydrazine t-BuN(H)NMe2 was synthesized via hydrazone and t-BuN(H)N(H)Me intermediates as the major component in a 90:5:5 mixture consisting of t-BuN(H)NMe2, t-BuN(Me)N(H)Me, and t-BuN(Me)NMe2. Reacting the mixture with n-BuLi followed by distillation and fractional crystallization led to the isolation of the ligand precursor LiN(t-Bu)NMe2. Lithium hydrazides, LiN(R)NMe2, were reacted with metal chlorides to afford the hydrazide complexes M(N(Et)NMe2)4 (M = Zr or Hf), MCl(N(R)NMe2)3 (M = Zr, R = i-Pr or t-Bu; M = Hf, R = t-Bu), and TaCl3(N(i-Pr)NMe2)2. The X-ray crystal structures of [LiN(i-Pr)NMe2]4, [LiN(t-Bu)NMe2.THF]2, ZrCl(N(R)NMe2)3 (R = i-Pr or t-Bu), and TaCl3(N(i-Pr)NMe2)2 were determined. The structural analyses revealed that the hydrazide ligands in ZrCl(N(R)NMe2)3 (R = i-Pr or t-Bu) and TaCl3(N(i-Pr)NMe2)2 are eta2 coordinated.     

Synthesis and X-ray structure of 1,1-dimethylhydrazinium azide

1,1-Dimethylhydrazinium azide, [ (CH₃)₂NH–NH₂] [N₃], was prepared in high yield from 1,1-dimethylhydrazine and HN₃ in CH₂Cl₂ solution at −20°C. The new compound has been fully characterized by elemental analysis, multinuclear NMR (¹H, ¹³C, ¹⁴ N, ¹⁵ N) and vibrational spectroscopy (IR, Raman). The structure in the solid state was determined by a low temperature (173 K) single crystal X-ray diffraction analysis.     

Synthesis of enamides from aldehydes and amides

A range of double unsaturated amides (15, 19, and 21), obtained by cross-coupling reactions was reacted with aldehydes to hemiaminals. Heating the hemiaminals in the presence of Ac₂O and pyridine affected clean conversion to the corresponding enamides, such as 42, 45, and 47. Alternatively, N,S-acetals were prepared which were oxidized to the sulfones. Treatment with base also gave the enamides, favoring the cis-isomer. However, this method is less general. Application of these methods led to the natural products lansiumamide-A (30_cis), lansiumamide-I (31) and lansiumamide-B (32).