Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 1. Isoindolobenzazepines, isoindolobenzazocines. (Review)

Data on methods for the construction of tetracyclic systems in which an isoindole ring is condensed with benzazepines and benzazocines on the [1,2] side are reviewed. The reaction conditions and approaches leading to isoindolobenzazepines and isoindolobenzazocines are discussed. Examples of the synthesis of physiologically active natural alkaloids with the structure of the above-mentioned condensed isoindoles are presented. Data for 1959–2004 are included. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 963–994, July, 2006.     

Synthesis of condensed thiazoles. (Review)

Data on the synthesis of thiazoles systems condensed with heterocycles are classified. The principal directions in the practical application of these substances are briefly discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 167–190, February, 2006.     

Synthesis and chemical transformations of 2,3-dihydropyrrole-2,3-diones annelated on the [a] side by azaheterocycles. (Review)

Data on methods for the synthesis of 2,3-dihydro-2,3-pyrrolediones condensed with azaheterocycles on the [a] side are reviewed. Their reactions with nucleophilic reagents, allylboronation, reduction, and thermal transformations are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–25, January, 2006.     

Development of the catalytic synthesis of compounds of the quinoline series (the N. S. Kozlov reaction) (Review)*

This article is dedicated to the 80^th anniversary of the Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus (in 1929-1959 the Institute of Chemistry, Academy of Sciences of the BSSR). It contains a review of the advances in the synthesis and properties of condensed heterocyclic systems containing a quinoline fragment – derivatives of quinaldine, benzo[f]quinoline, indeno- and indoloquinoline, benzo[a]phenanthridine, benzoacridine, tetrahydroquinoline, 1,7- and 4,7-phen-anthroline. The reactions forming the basis of the synthesis of the heterocycles are described – catalytic reaction of amines with acetylene, catalytic condensation of azomethines with methyl and α-methylene ketones, triple-component condensation of arylamines, carbonyl compounds, and CH acids.     

Derivatives of condensed thienopyrimidines 12. Synthesis of substituted pyrano(thiopyrano)-[4′,3′∶4,5]thieno[2,3-d]pyrimidines

A method for the synthesis of new condensed derivatives of 4-oxo-2-thioxo-5,6-dihydro-8H-pyrano(thiopyrano)[4′,3′∶4,5]thieno[2,3d]pyrimidines has been developed. It has been established that with increasing electron acceptor ability of the substituents on the nitrogen atom of the isothiocyanate starting materials there is a marked formation of 2-N'-thioureide derivatives of the condensed thiophenes. For Communication 11 see [1]. A. A. Mndzhoyan Institute of Fine Organic Chemistry, National Academy of Sciences, Republic of Armenia, Erevan 375014. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1388–1391, October, 1988.     

Condensed 1,2,3-triazoles (review)

Methods for the synthesis of condensed 1,2,3-triazoles, including mesoionic compounds, in the literature up to 2007 inclusively are presented. They are classified according to the method by which the molecular skeleton is formed. Mesoionic condensed compounds of the 1,2,3-triazole series are examined separately. Dedicated to Academician Boris Aleksandrovich Trofimov on his seventieth jubilee. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1295–1330, September, 2008.     

Synthesis of 2,3-disubstituted derivatives of pyrano-, thiopyrano-, and benzoannelated pyrido[2,3-<Emphasis Type="Italic">b</Emphasis>]thieno[3,2-<Emphasis Type="Italic">d</Emphasis>]pyrimidines

A new methods have been developed for the synthesis of condensed pyrido[2,3-b]thieno[3,2-d]pyrimidines based on cyclic derivatives of 4-cyanopyridine-3-thiones. The presence of two different reactive functional groups NH₂ and CONH gives the possibility of carrying out different conversions of thieno[2,3-b]pyridines. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, 1245–1252, August, 2008.     

Synthesis and Anticancer, Antiinflammatory,and Analgesic Activity Evaluation of Some Sulfa Drug and Acridine Derivatives

 Various sulfa drugs were condensed with 4-isothiocyanato-4-methyl-2-pentanone at pH∼3–5 by refluxing in methanol to give various substituted mercaptopyrimidines. On condensation with 9-chloro-2-substituted or -unsubstituted acridines, sulfathiazole gave the corresponding condensed products. N-Ethylaminoadenosine reacted with 9-chloroacridine to the coupled product. Condensation of sulfathiazole with 9-isothiocyanato-2,4-substituted or -unsubstituted acridines afforded the corresponding condensed compounds. The structures of all synthesized compounds were confirmed by spectroscopic methods. Anticancer, antiinflammatory, and analgesic activities of all compounds were investigated.     

Modified Coumarins. 16. Cyclohexane-Annelated Analogs of Pyranocoumarins

Modified derivatives of angular and linear pyranocoumarins containing a condensed cyclohexane moiety were prepared by fusing a 2,2-dimethyltetrahydropyran ring to the coumarin system and annelating a pyrone ring to derivatives of 2,2-dimethylchromane. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 313–318, July–August, 2005.     

Synthesis and Anticancer, Antiinflammatory,and Analgesic Activity Evaluation of Some Sulfa Drug and Acridine Derivatives

Summary.  Various sulfa drugs were condensed with 4-isothiocyanato-4-methyl-2-pentanone at pH∼3–5 by refluxing in methanol to give various substituted mercaptopyrimidines. On condensation with 9-chloro-2-substituted or -unsubstituted acridines, sulfathiazole gave the corresponding condensed products. N-Ethylaminoadenosine reacted with 9-chloroacridine to the coupled product. Condensation of sulfathiazole with 9-isothiocyanato-2,4-substituted or -unsubstituted acridines afforded the corresponding condensed compounds. The structures of all synthesized compounds were confirmed by spectroscopic methods. Anticancer, antiinflammatory, and analgesic activities of all compounds were investigated. Received November 18, 1999. Accepted (revised) January 12, 2000     

The notion of structure in modern chemistry. II. Structural variety of condensed phases. Generalized crystal chemistry

The structural variety of condensed phases with crystalline (c) or quasicrystalline (q) order or complete/partial disorder (d) is represented as a triangular diagram. The c, q, or d characteristic refers to one of the three dimensions so that the type of condensed phase is denoted by three symbols (ccc is the ideal crystal; cqd is a phase where disorder is combined with crystalline and quasicrystalline orders). Comparative studies of various condensed phases with data extrapolation to other states is termed generalized crystal chemistry. M. V. Lomonosov Moscow State University. Translated fromZhurnal Strukturnoi Khimii, Vol. 35, No. 3, pp. 99–102, May–June, 1994. Translated by L. Smolina     

Synthesis of imidazo[4,5-<Emphasis Type="Italic">b</Emphasis>]pyridines with a chiral substituent at the nitrogen atom and their conversion to piperazine derivatives

Imidazopyridine and benzimidazole derivatives have been prepared with chiral substituents at the nitrogen atom and have been converted to the corresponding condensed structures fused with a piperazine ring. A method has been developed for the synthesis of novel class of compounds – 6,7,8,9-tetra-hydropyrido[3',2':4,5]imidazo[1,2-a]pyrazine derivatives.     

Lactam acetals and acid amides. 32. Lactim-lactam tautomerization of condensed 4-pyridones

The tautomeric properties of a number of condensed 4-pyridone derivatives were investigated. The existence of lactim-lactam tautomerization in this series of compounds was established by IR and UV spectroscopy. It is shown that when α substituents are present in the 4-pyridone molecule, both intramolecular electronic effects and the effect of substituents on solvation of one or another tautomeric form and, consequently, on the position of the equilibrium should be taken into account. See [1] for communication 31. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 349–353, March, 1980.     

Functionalization of pyridines. 3. Reactions forming a carbon-heteroatom bond with group IV, V, and VI elements

The literature from the last 15–20 years on the synthesis of heteroatomic pyridine derivatives through the formation of pyridine carbon-heteroatom bonds is reviewed. Dedicated to Professor Henk van der Plas on his 70th birthday. For No. 2, see [1]. M. V. Lomonosov Moscow State University, Moscow 119899 Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 437–494, April, 1999.     

Photo-and thermochromic spiranes. 25. New indolinospiropyrans containing a condensed furan fragment

New indolinospirochromenes have been synthesized containing a condensed furan fragment, an analog of the methoxyl substituent in position 6′ of the chromene part of the molecule. Solutions of the obtained compounds display photochromic properties. For one of the compounds, depending on the temperature of irradiation, the cis-cisoid or trans-transoid isomer is fixed spectrally. An X-ray structural investigation has been carried out on crystals of spiropyrans possessing various forms of photoactivity in the solid phase. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 995–1005, July, 2006.     

Analysis of fenvalerate in its formulations and environmental samples using spectrophotometry

Two rapid, simple, sensitive, and nonextractive spectrophotometric methods were described for the determination of fenvalerate (syntheitic pyrethroid) in its formulations, water and grain samples. The methods are based on the hydrolysis of fenvalerate with methanolic NaOH to form 3-phenoxybenzaldehyde. The resultant aldehyde group was condensed with 4-aminoantipyrine in the basic medium to form a red product having λ_max at 489 nm or condensed with4,4′-methylene-bis-m-nitroaniline to form a plae red product with an absorption maximum of 513 nm. Beer’s law was obeyed over the range 0.6–10 μg/mL (molar absorptivity 2.184 × 10⁴ L/mol cm) for 4-aminoantityrine and over the range of 1–12 μg/mL (molar absorptivity 4.162 × 10⁴ L/mol cm) for 4,4′-methylene-bis-m-nitroaniline. The formations of color derivatives with the reagents are instantaneous and stable for 40 and 32 h, respectively. The methods were rapid, simple, sensitive, and free from nontarget species. The proposed methods have been applied to the determination of fenvalerate in its formulations and environmental samples. The text was submitted by the authors in English.     

Synthesis of α,α′-bis(R-benzylidene)cycloalkanones catalyzed by potassium hydrogen sulfate under solvent-free conditions

Cyclopentanone or cyclohexanone were condensed with aromatic aldehydes to give corresponding α,α′-bis(R-benzylidene)cyclopentanones or α,α′-bis(R-benzylidene)cyclohexanones. The reaction was catalyzed by potassium hydrogen sulfate with a yield of 84–95% under solvent-free conditions.     

A one-pot synthesis of alkyl acylcarbamodithioates from acid chlorides, thiols, and ammonium thiocyanate

Abstract  

An efficient synthesis of alkyl acylcarbamodithioates by reaction of acid chlorides with ammonium thiocyanate in the presence of thiols is described. The unusually large values of ⁵ J _FH = 12–15 Hz, observed for alkyl (2-fluorobenzoyl)carbamodithioates provide information about Ar–C–N–H torsion in these compounds.     

Thienopyridines: synthesis, properties, and biological activity

The current state and prospects of development of the chemistry of isomeric thienopyridines (synthesis, chemical transformations, and biological activities) are analyzed. Particular attention is given to studies published in the last 10–15 years. Dedicated to Academician V. I. Minkin on the occasion of his 70th birthday. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 847–885, April, 2005.     

XRF Analysis of Microsamples of Semiconductor Type Multielement Materials by the Thin Layer Method. Determination of Cr, Co, Ni, Cu, Zn, Ga, Se, Sb, Yb

 A simple and quick method of durable samples preparation by the thin layer method through direct digesting of the analysed material on the substrate has been presented. Four- and three-component mono- and polycrystals have been analysed. Standards have been used in calibration containing: Cr, Co, Ni, Cu, Zn, Ga, Se, Sb, Yb. To improve the correlation between the concentration and the fluorescent radiation models of mathematical corrections have additionally been used: multiple linear regression, Lucas-Tooth-Pyne model (L. T. P.) and de Jongh model (d. J.). Statistical parameters: detection limits for 0.5 mg samples: Cr–0.041%, Co–0.034%, Ni–0.042%, Cu–0.053%, Zn–0.054%, Ga–0.057%, Se–0.057%, Sb–0.113%, Yb–0.077%. Correlation coefficients: simple regression 0.9946–0.9997, multiple regression 0.9974–1.0000, L. T. P. 0.9993–1.0000, d. J. 0.9995–1.0000. Received August, 1, 1998. Revision March 25, 1999.