A. V. Butin

Furyl(aryl)methanes and their analogs. (Review)

The literature data on furyl(aryl)methanes are systematized and analyzed for the first time. Results obtained by the authors on the synthesis, reactions, and application of these compounds are reviewed.

Substituted 2-Formylbenzoic Acids in the Synthesis of 11H-Isoindolo[2,1-a]Benzimidazol-11-Ones, 5H-Isoindolo[2,1-a][3,1]Benzoxazine-5,11(6aH)-Diones, and 6,6a-Dihydroisoindolo-[2,1-a]Quinazoline-5,11-Diones

Optimal conditions were developed for the synthesis of 11H-isoindolo[2,1-a]benzimidazol-11-one, 5H-isoindolo[2,1-a][3,1]benzoxazine-5,11(6aH)-dione, and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in the reaction of substituted 2-formylbenzoic acids with o-phenylenediamine, anthranilic acid, and anthranilamide, respectively. The bifolded structure of 6,6a-dihydroisoindolo-[1,2-a]quinazoline-5,11-dione was verified and investigated.

Polyfuryl(aryl)alkanes and their derivatives. 17. Synthesis of compounds of the oxazulene series

Preparative methods were developed for the synthesis of various compounds of the benzofurooxazulene series. It was established that the formation of an oxazulenium salt and a dihydrooxazulene derivative during the treatment of 3-(5-methyl-2-furyl)-2-(3-oxobutyl)benzofurans with perchloric acid results from disproportionation of the intermediate compound—an oxazulene derivative.

Simple and Convenient Synthesis of 4-Unsubstituted-3- (3-Oxoalkyl)isocoumarins

Abstract A simple transformation of 2‐alkylfurans and 2‐formylbenzoic acids into 4‐unsubstituted 3‐(3‐oxoalkyl)isocoumarins is described. It is based on the synthesis of 2‐(2‐carboxybenzyl)furans followed by their acid‐catalyzed recyclization to the target isocoumarins.

Polyfuryl(aryl)alkanes and their derivatives 16. Convenient path to benzofuran ketones

Abstract2-(3-Oxobutyl)-3-(5-methyl-2-furyl)benzofurans were synthesized by the recyclization of 2-hydroxyarylbis(5-methyl-2-furyl)methanes in methanol saturated with hydrogen chloride. They can also be obtained by the reaction of salicylaldehydes and sylvane in an ethanol solution of hydrogen chloride.

Synthesis of pyrrolo[1,2-a][1,6]benzodiazonines from pyrrolo[1,2-a][1,4]benzodiazepines and alkynes containing electron-acceptor substituents

It has been established that the reaction of pyrrolo[1,2-a][1,4]benzodiazepines with activated alkynes gives pyrrolo[1,2-a][1,6]benzodiazonines as the products of diazepine ring expansion. In the case of pyrrolo[1,2-a][1,4]benzodiazepine, substituted with formyl group at the pyrrole ring, both expansion and cleavage of the diazepine fragment can occur.

Polyfuryl(aryl)alkanes and their derivatives

The reduction of 2-nitrophenyldifurylmethane with SnCl2 leads to an indolenyl ketone as a result of intramolecular heterocycloaddition of the intermediately formed nitroso derivative. During the reduction of 2-nitroaryldifurylmethanes in the Zn+HCl or NH2NH2·H2O+Pd/C systems, 2-aminoaryldifurylmethanes are formed; when treated with trityl perchlorate, their acetyl derivatives are converted into indolo[2,3-h]-1-oxazulenium perchlorates.

Transformation of 4-Substituted Tetrahydro-Pyrrolobenzodiazepines in a Three-Component Reaction With Methyl Propiolate and Indole

The three-component reaction of 4-phenyl-, p-methoxyphenyl-, and thienylpyrrolo[1,2-a][1,4]benzo-diazepines with methyl propiolate and indole in dichloromethane proceeds through opening of the diazepine ring. The major transformation products isolated are substituted pyrroles, namely, 1-(2-aminomethylphenyl)-5-(arylmethyl)-2-(indol-1(3)-yl)pyrroles and 1-(2-aminomethylphenyl)-2-aryl-(indol-3-yl)-methylpyrroles.

Acid-catalyzed cascade rearrangement of 4-acetoxy-9-furylnaphtho[2,3- b ]furans

Acid-catalyzed recyclization of 4-acetoxy-9-furylnaphtho[2,3-b]furans efficiently produced naphtho[1,2-b:3,4-b’]difurans. On the other hand, 4-aminonaphtho[2,3-b]furans failed to undergo the analogous recyclization into benzo[g]furo[2,3-e]indoles. The difference in behavior of these two types of substrates was explained by employing density functional theory calculations.Graphical abstract

Furfuryl aryl(alkyl) ketones: preparation and synthetic potential (review)

Methods for the synthesis of furfuryl aryl(alkyl) ketones, published from 1985 to 2011, have been reviewed. The synthetic potential of these compounds is presented.