A. V. Turov

Phosphorylation of 1,3-Di(N-alkyl)Azoles by Phosphorus(V) Acid Chlorides — a Route to Potential Haptens Derived from Phosphinic Acids

Abstract Phosphorylation of N-alky lated imidazoles and benzimidazoles at C-2 by CH3POCl2, PhPOCl2-POCl3 in pyridine-triethylamine solution is described. The formed heteroaryl-substituted phosphinic or phosphonic acid chlorides were transformed without isolation into the corresponding phosphinic (phosphonic) acids, their salts or amides with moderate yields This reaction opens a simple way to potential haptens derived from phosphinic acids These haptens mimic tetrahedral transition state of many reactions and can be used to obtain catalytic antibodies The functionalized heteroarylsubstituted phosphinic acids which have been used as hapten precursors were obtained by phosphorylation of 1-alkyl-5-nitrobenzimidazole or by usage of a new phosphorylating reagent —(4-trichloromethylphenyl)phosphonic dichlonde

Synthesis of Fused Imidazoles Based on γ‐Bromodypnone

Abstract A new method based on the reaction of 4‐bromo‐1,3‐diphenyl‐2‐buten‐1‐one with heterocyclic amines was proposed for the synthesis of fused imidazoles.

Synthesis of Fused Pyrido[ a ]imidazoles

Abstract A new method based on the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one with imidazoles and benzimidazoles was proposed to obtain imidazo[1,2-a]pyridinium and pyrido[2,1-b]benzimidazolium salts.

4-Hydroxy-2-quinolones. 32. Synthesis and antithyroid activity of thio analogs of 1H-2-oxo-3-(2-Benzimidazolyl)-4-hydroxyquinoline

We propose preparative synthesis methods for 2-thio-4-hydroxy-, 2-oxo-4-mercapto-, and 2-thio-4-mercapto-1H-3-(2-benzimidazolyl)quinolines. We have studied the antithyroid activity of the synthesized compounds.

4-hydroxy-2-quinolones. 22.* Synthesis and biological properties of 1-alkyl(aryl)-2-oxo-3-carbethoxy-4-hydroxyquinolines and their derivatives

The presently known method for obtaining ethyl esters of 1-alkyl(or aryl)-2-oxo-4-hydroxyquinoline-3-carboxylic acids and their derivatives has been improved. Results are presented from an investigation of the anticoagulant, analgesic, and antiinflamatory activities of the synthesized compounds.

Criteria for establishment of three-dimensional structures of Diels-Alder adducts in the isoindole series. 2. Reaction of 1,2-disubstituted isoindoles with maleinimide derivatives

The Diels-Alder reaction of a series of 1,2-disubstituted isoindoles with maleinimide derivatives under conditions of kinetic and thermodynamic control was investigated. Criteria for the establishment of the three-dimensional structures of the adducts obtained were found. The possibility of supra-antara cycloaddition and the formation of 1∶2 adducts was demonstrated.

4-hydroxy-2-quinolones. 118*. Synthesis, structure, and chemical properties of 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo-[3,2-a]quinoline-4-carboxylic acid and its ethyl ester

Bromination of N-allyl-substituted 4-hydroxy-2-quinolinones with molecular bromine in acetic acid or carbon tetrachloride occurs with closing of a five membered oxazole ring to give 2-bromomethyl-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline.

Recyclization of 2-imino-2h-1-benzopyrans under the influence of nucleophilic reagents. 1. New approach to the synthesis of 3-(1,3,4oxadi-, thiadi-, and triazolyl-2)coumarins

It has been found that under the action of hydrazides of carboxylic acids, 2-iminocoumarin-3-carboxamides are recyclized to N(1)-acylamidrazones of coumarin-3-carboxylic acids. The use of N(1)-acylamidrazones is proposed as a simple and effective means of synthesizing 3-(1,3,4-oxadi-, thiodi-, and triazolyl-2)coumarins. The possibilities of alternate schemes of synthesis are discussed, and a mechanism is suggested for the recyclization.

4-Hydroxy-2-quinolones. 23. N-(2-thiazolyl)amides of 1-R-2-oxo-4-hydroxyquinoline-3-carboxylic acids — A new group of potential antiinflammatory agents

By thermolysis of equimolar quantities of 1-R-2-oxo-3-carbethoxy-4-hydroxyquinolines and 2-aminothiazole in diphenyl oxide, we have synthesized N-(2-thiazolyl)amides of 1-R-2-oxo-4-hydroxyquinoline-3-carboxylic acids. some of the substances that were obtained have high antiexudative activity (carrageenan edema), higher than the activity of sudoxicam.

4-Hydroxy-2-quinolones 7. Synthesis and biological properties of 1-R-3-(2-benzimidazolyl)-4-hydroxy-2-quinolones

Condensation of 1-R-3-carbethoxy-4-hydroxy-2-quinolones with o-phenylene diamine gives the corresponding 1-R-3-(2-benzimidazolyl)-4-hydroxy-2-quinolones. Data on a study of the antithyroid activity of the synthesized compounds is presented.