Synthesis and transformations of 2-(2-furyl)- and 2-[β-(2-furyl)vinyl] phenanthr [9,10]imidazoles

The corresponding 2-(2-furyl)- and 2-[-(2-furyl)vinyl] phenanthr[9,10]imidazoles were obtained by the condensation of 9,10 phenanthrenequinone with furfural, -(2-furyl)acrolein, and their 5-bromo and 5-nitro derivatives in the presence of ammonium acetate in glacial acetic acid. Their metallation, acetylation, nitration, and replacement of halogen by a nitro group were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1014–1016, August, 1971.     

Stereochemical studies of 5-methyl-3-(substituted phenyl)-5-[(substituted phenyl) hydroxy methyl]-2-thiooxazolidin-4-ones

The synthesis and stereochemical aspects of the aldol products, 5-methyl-3-(substituted phenyl)-5-[(substituted phenyl) hydroxy methyl]-2-thiooxazolidin-4-ones, are discussed.     

Synthesis and transformations of 2-(2-furyl)- and 2-[β-(2-furyl)vinyl]imidazo[4,5-f]quinolines

The corresponding 2-(2-furyl)- and 2-[-(2-furyl)vinyl]imida zo[4,5-f]quinolines were obtained by condensation of 5,6-diaminoquinoline and 5-amino-6-rnethylaminoquinoline with furfural, furylacrolein, and their 5-bromo and 5-nitro derivatives and also with the hydrochlorides of imino esters of furancarboxylic and furylacrylic acids. Alkylation, acetylation, nitration, and substitution of the halogen in the furan ring by a nitro group were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 440–442, April, 1973.     

Synthesis and transformations of 2-(2-furyl)-and 2-[β-(2-furyl)vinyl]imidazo[4,5-b]phenazines

The corresponding 2-(2-furyl)- and 2-[-(2-furyl)vinyl]imidazo[4,5-b]phenazines were obtained by the condensation of 2,3-diaminophenazine with furfural and 2-furylacrolein and with their 5-bromo and 5-nitro derivatives. The phenazines were also synthesized by the reaction of 2-methylimidazo[4,5-b]phenazine with furfural and 5-bromo- and 5-nitrofurfural. The alkylation, acetylation, and nitration of the compounds obtained, as well as replacement of the halogen in the furan ring by a nitro group, were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1425–1428, October, 1971.     

Synthesis and transformations of 2-(2-furyl)-and 2-[β;-(2-furyl)vinyl]naphth[1,2-d]imidazoles

The corresponding 2-(2-furyl)naphth[1,2-d]imidazoles were obtained by heating Schiff bases, prepared from 1,2-naphthalenediamine and furfural and 5-bromo- and 5-nitrofurfurals, in nitrobenzene. 2-[-(2-Furyl)vinyl]naphth[1,2-d]imidazoles were synthesized by condensation of 2-methylnaphth[1,2-d]imidazole with furfural and 5-bromo- and 5-nitrofurfural. The methylation, nitration, and acetylation of the compounds obtained were studied, and the replacement of the bromine atom in the furan ring by a nitro group was also investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1555–1557, November, 1972.     

Preparations of bis[2-(2-arylethynyl)-3-thienyl]arenes and bis[2-{2-(trimethylsilyl)ethynyl}-3-thienyl]arenes

4,4′-Bis[2-(2-phenylethynyl)-3-thienyl]biphenyl, 4,4′-bis[2-{2-(trimethylsilyl)ethynyl}-3-thienyl]biphenyl and their congeners were prepared and their properties were studied. Extension of π-system through the central benzene ring was suggested by UV-vis spectra. Connection of two 1,4-bis[2-{2-(trimethylsilyl)ethynyl}-3-thienyl]benzene units was exemplified.     

4-(Azulen-1-yl) six-membered heteroaromatics substituted in 2- and 6- positions with 2-(2-furyl)vinyl, 2-(2-thienyl)vinyl or 2-(3-thienyl)vinyl moieties

The synthesis of pyrylium and pyridinium salts and pyridines with azulene-1-yl moieties in position 4 and two 2-heteroarylvinyl groups in positions 2 and 6 was accomplished. The pyrylium salts were obtained starting from pyranones and pyridines could be prepared from these salts by treating them with ammonium acetate. The general procedures for the synthesis of pyridinium salts, which occur with good results in less delocalized electronic systems, do not take place when applied to the above obtained pyrylium salts. Therefore, as starting material 4-(azulen-1-yl)-1-(n-butyl)-2,6-dimethylpyridinium perchlorate was used, which was condensed with heteroarylcarboxaldehydes. These compounds were completely characterized and some of their spectra were discussed. Their interaction with some metal ions was revealed, observing an affinity better than in the case of simple azulenepyridines. In the last part of the paper are presented redox potentials for several pyrylium salts and pyridines in comparison with those of the nonvinylogated derivatives.     

Synthesis of some substituted 2- and 4-[2′-(5″-nitro-2″-furyl)vinyl]-quinolines

A series of 2- and 4-[2-(5-nitro-2-furyl)vinyl]quinolines were synthesized by catalytic condensation of 5-nitrofurfural with 2- and 4-methylquinolines. 2-Methylquinoline (quinaldine) and its substituted derivatives also react when the starting reagents are fused directly.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 253–255, February, 1976.     

Indole Derivatives. 142. Some Properties of [4-(2-Indolyl)phenyl]phenylmethane and 1-[4-(2-Indolyl)phenyl]-2-phenylethane

The reactions of 2-arylindoles with strong electrophiles take place with significant resin formation. It was shown that electrophilic substitution is directed into the indole ring and into the side chain. 1,7-Migration of the substituent is observed in the investigated systems.     

β-(2-furyl and 2-thienyl)acroleins in reactions with vinyloxyanilines

Equimolecular amounts of-(2-furyl and 2-thienyl)acroleins and o-, m-, and p-vinyloxy-anilines react at room temperature to form-(2-furyl and 2-thienyl)acrylidinevinyloxy-anilines. Their structures were proved by hydrogenation, hydrolysis, and IR spectroscopy. Their capacity for complexing with hydrated stannic chloride was established. The bacteriostatic activity of some of the synthesized substances was tested.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1626–1630, December, 1971.     

Synthesis of 2-phenyl-3-(2-furyl) — and 2-phenyl-3-[β-(2-furyl)vinyl]-1,2-dihydro-naphtho[1,2-d]-1,2,4-triazines

The corresponding 2-phenyl-3-(2-furyl)- and 2-phenyl-3-[-(2-furyl)vinyl]-1,2-dihydronaphtho-[1,2-d]-1,2,4-triazines were obtained by heating Schiff bases [prepared by reaction of 1-(phenyl-azo)-2-aminonaphthalene with furfural, -(2-furyl)acrolein, and their 5-bromo and 5-nitro derivatives] in glacial acetic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 158–160, February, 1973.     

2-[2-(4,6-二甲氧基嘧啶-2-氧)苯基]-2-(取代苯胺)乙氰类化合物的合成及除草活性研究

以水杨醛为原料,所得中间体2-(4,6-二甲氧基嘧啶-2-氧基)苯甲醛经三组分反应合成了12个2-[2-(4,6-二甲氧基嘧啶-2-氧基)苯基]-2-(取代苯胺)乙氰类化合物,通过1H NMR,MS和元素分析对所合成的化合物进行了结构表征.初步生物活性测试结果表明,在试验浓度下合成化合物均具有良好的除草活性.     

新型N-[2-(取代苯并噻唑-2-氨基甲酰基)苯基]取代氟基苯甲酰胺的合成及其抗癌活性

2,4-二氟苯甲酸或2-氟苯甲酸与二氯亚砜经酰氯化反应,再与邻氨基苯甲酸反应后在醋酸酐中闭环,最后与取代苯并噻唑胺反应合成了9个新型的N-[2-(取代苯并噻唑-2-氨基甲酰基)苯基]取代氟基苯甲酰胺(6a～6i),其结构经1H NMR,13C NMR,IR和元素分析表征。采用MTT法对6a～6i进行抑制PC3癌细胞体外活性测试,结果表明6a～6i具有不同程度的抑制PC3癌细胞活性,其中10μmol.L-16b对PC3的抑制率为69.9%。     

Synthesis and X-ray structures of dinitrato-bis[2-(2′-thienyl)-1-(2′-thienylmethyl)benzimidazole]copper(II) and dichloro-bis-[2-(2′-thienyl)-benzimidazole]copper(II)-ethanol

Summary The reactions of Cu(NO₃)₂ · 3 H₂O with 2- (2-thienyl)-1-(2-thienylmethyl)benzimidazole (L) and of CuCl₂ · 2H₂O with 2-(2-thienyl)benzimidazole (L) have been carried out. The crystal structure of two isolated complexes,(1) and(2), have been determined by single-crystal x-ray diffraction methods. Crystals of(1) are monoclinic, space groupP2₁ /c, witha=9.884(4),b=9.892(4),c=18.732(8) Å, =114.89(2)°,Z=2;R=0.068 for 1909 observed reflections. Crystals of (2) are orthorhombic, space groupPbcn, witha=14.835(1),b=8.193(1),c=20.493(1) Å,Z=4;R=0.086 for 415 observed reflections. In the complex (1) the copper co-ordination is tetragonal (compressed octahedral) and involves a nitrogen atom of the organic ligand [Cu-N 1.970(6) Å] and two oxygen atoms of the nitrate group [Cu-O 2.318(7) and 2.246(9) Å] which appears to coordinate nearly symmetrically to the metal; however it has unusually large thermal motion which suggests a fluxional behaviour. In the complex (2) the co-ordination is square planar and involves an imidazole nitrogen [Cu-N 1.95(3) Å] and a chlorine atom [Cu-Cl 2.27(1) Å]. A long interaction Cu-S=3.37(2) Å completes the co-ordination polyhedron to a very elongated distorted tetragonal bipyramid. In both compounds a thiophene ring is disordered.     

Nitration of 2- and 4-[2-(2-furyl)vinyl]thiazole derivatives

Nitration of 4-methyl-2-[2-(nitro-2-furyl)vinyl]thiazole with a mixture of concentrated nitric and sulfuric acids leads to 4-methyl-5-nitro-2-[2-(3,5-dinitro-2-furyl)vinyl]thiazole. Under the same conditions 2-methyl- and 2-acetamido-4-[1-R-2-(5-nitro-2-furyl)vinyl]thiazoles (R=CH₃, Cl) are nitrated in the 3 position of the furan ring, 2-amino-4-[1-chloro-2-(5-nitro-2-furyl)vinyl]thiazole is nitrated in the 5 position of the thiazole ring and 2-acetamido-5-nitro-4-[2-(2-furyl)vinyl]thiazole undergoes profound changes. Under the influence of a mixture of of nitric acid and acetic anhydride the latter compound is converted quantitatively to the 5-nitro derivative (with respect to the furan ring), whereas 4-[2-(5-nitro-2-furyl)vinyl]thiazole derivatives do not undergo reaction.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 314–317, March, 1977.