Synthesis and X-ray diffraction studies of 3-cyano-2-trifluoromethyl-4H-pyrido[1,2-a]pyrimidine derivatives

Reactions of 2-chloro-1-cyano-2-trifluoromethylethylenes with 2-aminopyridines were studied. According to the data of NMR spectroscopy and X-ray diffraction analysis, the first stage of the reaction involves alkenylation of the exocyclic nitrogen atom of 2-aminopyridines followed by formation of pyrido[1,2-a]pyrimidines. Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1261–1264, July, 2000.     

Synthesis and X-ray structural investigation of 6-chloro-10-phenyl-1,2,3,4-tetrahydroacridine

An X-ray structural study of 6-chloro-10-phenyl-1,2,3,4-tetrahydroacridine prepared by the reaction of cyclohexanone with 2-amino-5-chlorobenzofenone was carried out. At 20°Ca=24.215(6),b=8.967(2),c=15.006(3) Å, =115.57(2)°,V= 2939(1) ų,d _calc=1.310 g cm^–3,Z=4, space groupC2/c, 1324 reflections, MoK,R=0.038. The cyclohexene ring has a half-chair conformation. The phenyl substituent is rotated 71.2° with respect to the plane of the quinoline fragment.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1467–1468, August, 1994.     

X-Ray diffraction structural study of the endo,trans dimer of 2-chloro-3-phenyl-1-indenone

An x-ray diffraction structural analysis showed that the product of the dimerization of 2-chloro-3-phenyl-1-indenone is the endo,trans-[2+2] cycloadduct.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 204–207, January, 1991.     

An unexpected and efficient synthesis of 3-chloro-4-cyanopyridine

Reaction of 4-cyanopyridine N-oxide with phosphorus oxychloride/phosphorus pentachloride gave 3-chloro-4-cyanopyridine in good yield in sharp contrast to the expected chlorination in the 2-position. A mechanistic interpretation of the results is proposed involving a chloride attack at the 4-position as the main feature.     

Synthesis of 2-alkyl-6-phenyl-3, 4-c cycloheptenopyrylium salts

A method is given for synthesizing 2-alkyl-6-phenyl-3, 4-cycloheptenopyrylium perchlorates, obtained in 45–55% yields by acylating cycloheptenylacetophenone with anhydrides of aliphatic acids in the presence of 70% perchloric acid. Treatment of the pyrylium salts with ammonia gives a good yield of 2-alkyl-6-phenyl -3, 4-cycloheptenopyridine.     

Synthesis and properties of 2-imino-3-benzyl-5-phenyl-1, 3, 4-oxadiazoline

2-Imino-3-benzyl-5-phenyl-1, 3, 4-oxadiazoline (Ia) was synthesized by the reaction of benzyl chloride with 2-amino-5-phenyl-1, 3, 4-oxadiazole (II). A number of imino-group derivatives of Ia were prepared. The structure of the compounds prepared were confirmed by means of their IR spectra.     

Molecular structure of 1-phenyl-2-trifluoromethyl-3-benzoylaziridine

1-Phenyl-2-trifluoromethyl-3-benzoylaziridine has been studied by X-ray structural analysis. Protons of the aziridine cycle are intrans positions. The C(1)-N(1) bond is the shortest of the corresponding bonds in aziridine derivatives, which have been studied by X-ray structural analysis previously.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1975–1977, October, 1995.     

5-芳胺-6-氯-2, 3-二氰吡嗪的合成

本文以丙二腈为起始原料, 经过六步合成了中间体7, 化合物7和芳胺发生单取代得到目标产物5-芳胺-6-氯-2, 3-二氰吡嗪(8), 所合成的这10个目标产物文献上未见报道的, 通过了元素分析, IR, 1HNMR, MS证实其结构。粉末法测试表明它们都具有一定的二阶倍频效应。     

5-取代苯胺基-6-苯基-1, 2, 4-三嗪-3-硫酮的合成

苯甲酰基-N-取代苯基硫代甲酰胺和氨基硫脲反应, 首先在酸性介质中形成缩氨基硫脲, 然后在碱性介质(pH=8~9)中环化, 生成5-取代苯胺基-6-苯基-1, 2, 4-三嗪-3-硫酮。本文合成10个新的该类杂环化合物。     

Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydoxy-4-phenyl-3-cyano-2-pyridone dyes

ABSTRACT: BACKGROUND: A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using classical reaction for the synthesis of the azo compounds. RESULTS: The structure of the dyes was confirmed by UV-vis, FT-IR, 1H NMR, 13C NMR spectroscopic technique and elemental analysis. The solvatochromic behaviour of the dyes was evaluated with respect to visible absorption properties in various solvents. CONCLUSIONS: The azo-hydrazone tautomeric equilibration is found to depend upon substituents as well as on solvents. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data.     

Synthesis and fungicidal activity of new 4-hydroxy-6-trifluoromethyl-2-phenylindoles

Starting from 1,3-dinitro-5-trifluoromethylbenzene, a pioneering synthesis and dimethylaminomethylation of new 2-aryl- 4-hydroxy-6-trifluoromethylindoles have been performed. The study of fungicidal activity has revealed the effect of dimethylaminomethyl group position on fungitoxic properties.     

Synthesis and regioselective cycloaddition reaction of 2,4,6-triazido-3-chloro-5-cyanopyridine with norbornene

Treatment of 3-cyanotetrachloropyridine with sodium azide gives 2,4,6-triazido-3-chloro-5-cyanopyridine. This compound reacts regioselectively with norbomene to form an aziridinyl cydoadduct only at the azido group in position 4 of the pyridine ring.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1650–1652, December, 1993.     

Synthesis and X-ray crystallographic investigation of 3-phenyl-3-phenoxymethyl-2-oxazolidinone

Conclusions 3-Phenyl-5-phenoxymethyl-2-oxazolidinone is the product of interaction of phenylisocyanate with phenylglycidyl ether. Its molecule has a less strained conformation than the molecule of related 2-N-phenylimino-3-phenyl-5-phenoxymethyloxazolidine.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 870–874, April, 1986.     

Reaction of ketenes with N,N-disubstituted α-aminomethyleneketones VIII. Synthesis of N,N-disubstituted 4-amino-3-chloro-6-phenyl-2H-pyran-2-ones

The dipolar 1,4-cycloaddition of dichloroketene to N,N-disubstituted 3-amino-1-phenyl-2-propene-1-onesled directly to N,N-disubstituted 4-amino-3-chloro-6-phenyl-2H-pyran-2-ones only in the case of an usual aliphatic N,N-disubstitution. In the case of partial or full aromatic N-substitution, N,N-disubstituted 4-amino-3,3-dichloro-3,4-dihydro-6-phenyl-2H-pyran-2-ones were instead obtained, which were dehydrochlorinated with DBN to the corresponding 4-amino-3-chloro-6-phenyl-2H-pyran-2-ones.     

1,2,5-Trimethyl-4-aminopiperidine and 3, 6-dimethyl-4-phenyl-2-aminopyridine

1,2,5-Trimethylpiperid-4-one is used to prepare 1, 2, 5-trimethyl-4-aminopiperidine, which is then converted to 1, 2, 5-trimethyl-4-(diethylaminoacetylamino)piperidine. Amination of 2, 5-dimethyl-4-phenylpyridine is effected, and 3, 6-dimethyl-4-phenyl-2-aminopyridine is thereby obtained.     

Solvent and temparature dependent regioselective reactions between 2-chloro-6-cyanopyridine and aliphatic alcohols

Reaction of 2-chloro-6-cyanopyridine with aliphatic mono- and di-alcohols or ethylene glycols affords, depending on the reaction conditions, alkoxypyridines or imino ester pyridines or a mixture of both types of compounds. It is suggested that the product distribution is determined by the stability of an imidate anion formed as an intermediate. An improved synthesis of 2-chloro-6-cyanopyridine is also described.     

X-ray diffraction and spectral studies of 1-phenyl-3-methyl-4-(2′,4′-Dimethylphenylazo)-pyrazolone-5

The molecular and crystal structures of 1-phenyl-3-methyl-4-(2,4-dimethyl-phenylazo) pyrazolone-5 were determined. In the crystal the molecule exists as the hydrazone tautomer. The pyrazole ring is planar, and the substituents are practically coplanar with it. The molecule contains an intramolecular NH...O hydrogen bond that closes a practically planar six-membered ring (N...O, 2.77 (I), H...O 2.14 Å, angle at H(N(4)) hydrogen 131 °). The x-ray diffraction data agree with the spectral data and with the CNO calculation.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 816–821, June, 1985.