An unusual reaction of 2-(2-pyridylcarbonyl)- and 2-(2-quinolylcarbonyl)benzoyl chlorides with p-nitroaniline

In the reaction of 2-(2-pyridylcarbonyl)benzoyl chloride, which exists in the form of 6,11-dioxo-6,11dihydrobenzo[b]quinolizinium chloride, with p-nitroaniline, 2-(4-nitrophenylimino)-6, 11-dihydro-2H-benzo-[b]quinolizine-6, I I -dione is unexpectedly formed. When it reacts with water or methanol there is an opening of the quinolizine ring and aromatization of the quinoid fragment with the formation of 2-[4-(4nitrophenylamino)-2-pyridylcarbonyl]benzoic acid or its methyl ester. Under the action of antimony pentachloride, 2- 2-quinolylcarbonyl)benzoylchloride-3 (2-quinolyl)-3-chloro- 1, 3-dihydrobenzo[c]furan-1 -one -is converted to 3-(2-quinolyl)-1,3-dihydrobenzo[c]furan-1-on-3-ylium hexachlorantimonate, which undergoes isomerizing recyclization upon heating to 7,12-dioxo-7,12-dihydrobenzo[b/ hexachloroantimonate. The latter enters into an analogous reaction with p-nitroaniline, thereby forming 5-(4-nitrophenylimino)-7,12-dihydro-5H-dibenzo[b,f]quinolizine-7,2-dione.Riga Technical University, Riga LV-1048. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 938–944, July, 1995. Original article submitted May 31, 1995.     

Regioselectivities in deprotonation of 2-(4-chloro-2-pyridyl)benzoic acid and corresponding ester and amide

Upon treatment of ethyl 2-(4-chloro-2-pyridyl)benzoic acid, 2-(4-chloro-2-pyridyl)benzoate, and N,N-diisopropyl-2-(4-chloro-2-pyridyl)benzamide with LTMP at −75 °C in THF, the lithio derivatives at C5′ are generated regiospecifically, as demonstrated by subsequent quenching with electrophiles. The lithio derivative at C3′ is only evidenced from the benzamide at higher temperature (−50 °C), when treated with LTMP in THF; it instantly cyclizes to 1-chloro-4-azafluorenone. The latter is converted to onychine, an alkaloid endowed with anticandidal activity.     

Synthesis and ring-chain isomerism of n-monosubstituted 4-benzoylnicotinamides and 3-benzoylisonicotinamides

4-Benzoylnicotinoyl and 3-benzoylisonicotinoyl chlorides have been found to exist in cyclic forms (3-chloro-3-phenyl-6(or 5)-azaphthalides), and their benzyl-amides also occur as the cyclic forms (azaisoindolinones). The tert-butylamides of both acids are obtained in the open amide forms. It has been shown by PMR that N-tert-butyl-4-benzoylnicotinamide displays a greater tendency to undergo closure of the isoindolinone ring (K_T = 0.24 in CD₃OD) than does N-tert-butyl-3-benzoylisonicotinamide (K_T = 0).Translated from Khimiya Gererotsiklicheskikh Soedinenii, No. 1, pp. 80–83, January, 1986.     

Synthesis and properties of 2-(2-pyridyl)-1-azaazulene

The title azaazulene 3 was synthesized either by reaction of tropone with N-{(2-pyridyl)acetyl}pyridinium iodide in the presence of ammonium acetate or by palladium-catalyzed cross-coupling between 2-halo-1-azaazulene and 2-substituted pyridine. The compound shows relatively stronger basicity compared with 2,2′-bipyridyl. While 3 showed no emission from the S₁ state but from the S₂ state like azulene does, the protonated species of 3 exhibited emission from the S₁ state. Cationic metal-dependent absorption and emission relating to complexation were also studied.     

One-pot synthesis of 2-（1-acyloxypentyl） benzoic acids

A one-pot synthesis of 2-（1-acyloxypcntyl） benzoic acids by trapping the carboxylatc/alkoxide dianion with acylating reagents following Grignard addition with n-BuMgBr to 2-formylbcnzoic acid was described. Compared with routine synthetic method, this novel procedure has the advantage of convenient operation and higher yields.     

Synthesis of dialkyl esters of arylamino(2-pyridyl)methyl-phosphonic acids

Crystalline dialkyl esters of arylamino(2-pyridyl)methylphosphonic acids have been synthesized by the reaction of 1-pyridylazomethines with dialkyl phosphites in the presence of sodium alkoxides. When -pyridinealdehyde was condensed with dialkyl phosphites in the presence of sodium alkoxides, dialkyl esters of hydroxy(2-pyridyl) methylphosphonic acids were obtained in the form of viscous liquids. These compounds were identified in the form of the crystalline methiodides.     

Synthesis and structure of amides of 4-aryl(hetaryl)-2-pyrrolidone-3-carboxylic acids

Amides of 4-aryl(hetaryl)-2-pyrrolidone-3-carboxylic acids have been prepared via ammonolysis of the corresponding esters of pyrrolidone carboxylic acids. The products structure has been characterized by means of IR, ¹H NMR, ¹H–¹³C HMQC, and HMBC spectroscopy.     

Synthesis and complexing ability of 2-(2-ethoxycarbonyl-3-oxo-3-polyfluoroalkylprop-1-enylamino) benzoic acids

The condensation of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates with 2-aminobenzoic acid occurs at the ethoxymethylidene substituent and gives 2-(2-ethoxy-carbonyl-3-oxo-3-polyfluoroalkylprop-1-enylamino)benzoic acids. These compounds serve as new O,N,O-tridentate ligands capable of forming nickel(ii) and copper(ii) complexes.     

Synthesis and metallation of 2-(pyridyl)benzoic acids and ethyl 2-(pyridyl)benzoates: a new route to azafluorenones

The ring deprotonation of 2-(2- and 4-pyridyl)benzoic acids using lithium dialkylamides in THF at rt, and the in situ cyclization afforded 4- and 2-azafluorenones, respectively. 1-Azafluorenone was obtained from ethyl 2-(3-pyridyl)benzoate using a similar protocol.     

Synthesis and spectral and luminescent properties of 4-(5-aryloxazoyl-2)benzoic acids and their derivatives

Condensation of acid chloride of monomethyl terephtalate with -aminomethyl-arylketones and subsequent cyclodehydration of the resulting amides in sulfuric acid or phosphorus oxychloride give rise to methyl 4-(5-aryloxazolyl-2)benzoates which led to the corresponding acids, acid chlorides, and amides. The effect of electron-withdrawing groups on the spectral and luminescent properties, as well as on the stability of substituted 2,5-diaryloxazoles toward UV irradiation has been investigated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1261–1264, September, 1986.     

Synthesis of maleopimaric and citraconopimaric acids N-[3-(pyrimidin-2-yl)aryl]amides

Acylation of 6-methyl-N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine, 4-methyl-N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine, and N-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine with maleopimaric and citraconopimaric acid chlorides, with benzotriazolyl maleopimarate afforded N-[3-(pyrimidin-2-yl)aryl]amides of maleopimaric and citraconopimaric acids. By the reaction of substituted N-arylamides of maleopimaric acid with methanesulfonic acid biologically active methanesulfonates were obtained.     

1-(2-氯-4-吡啶基)-3-苯基脲的合成

氯氨基吡啶;氯吡啶基苯基脲;1-(2-氯-4-吡啶基)-3-苯基脲的合成     

Synthesis,polarography and herbicidal activity of quaternary salts of 2-(4-pyridyl)-1,3,5-triazines, 5-(4-pyridyl)pyrimidine, 2-(4-pyridyl)pyrimidine and related compounds

2-(4-Pyridyl)-1,3,5-triazine, 2-(4-pyridyl)-4-methyl-1,3,5-triazine, 2-(4-pyridyl)-4,6-dimethyl-1,3,5-triazine and 2-(4-pyridyl)pyrimidine have been prepared by modification of established triazine and pyrimidine syntheses. These compounds and some of their relatives have been converted to quaternary pyridinium salts. The polarographic reduction potentials of the salts in aqueous solution are pH dependent. The activity of the salts as post-emergent herbicides is reported.     

Synthesis of amides of 2-oxoquinolincarboxylic acids

The reaction of aryl amides of monoefhyl malonate with 2-aminobenzaldehyde in ethanol in the presence of catalytic amounts of base is found to give aryl amides of 2-oxoquinolin-3-carboxylic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 89–91, January, 1992.     

Sulfur-containing carboxylic acids. Communication 3. Synthesis of β-(acetylthio)alkanoic acids amides

Conclusions Amides of -mercapto- or -(acetylthio)alkanoic acids were obtained by the reaction of -thiolactones or -(acetylthio)alkanoic acid chlorides with amines.For Communication 2, see [1].Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 616–621, March, 1983.     

(O-Si)-Chelate acetic and benzoic acid N-(fluorosilylmethyl)amides: synthesis and structure

Russian Chemical Bulletin - New representatives of (O-Si)-chelate compounds, N-(fluorosilyl)methyl derivatives of N-methylacetamide, N-methylbenzamide, N-phenylacetamide, and N-phenylbenzamide,...