Formation of pyrrolo[2,3-f]quinolines from substituted 5-methyl-6-aminomoles by the combes reaction

It is shown that the reaction of 2, 3, 5-trimethyl-6-amino-indole with 1, 3-diketones is a convenient method for the preparation of angular IH-pyrrolo[2,3-f]quinolines, while the presence of a methyl group on the pyrrolic nitrogen atom of the initial indole as a result of steric hindrance completely blocks cyclization to the corresponding pyrroloquinolines.Mordovskii State Educational Institute, Saransk 430007. Moscow State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No 11, pp. 1499–1501, November, 1995. Original article submitted May 23, 1995.     

Traditional and modern approaches to the synthesis of quinoline systems by the Skraup and Doebner-Miller methods. (Review)

Recent data on classical and modified methods for the synthesis of quinoline systems by the Skraup and Doebner-Miller reactions, not included in reviews on heterocycles, are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 803–824, June, 2006.     

1,2,3-Trimethyl-5-aminoindole in reactions with acetoacetic ester and ethoxymethylene-malonic ester

A method is proposed for obtaining N-methylpyrrolo[3,2-flquinolines with functional groups on the pyridine ring. M. E. Evsev'ev Mordovian State Pedagogical Institute, Saransk 430007. M. V. Lomonosov Moscow State University, Moscow 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1486–1489, November, 1997.     

Using of 4-amino-2-phenylindoles in the synthesis of pyrroloquinolines by the combes reaction

The reaction of 4-amino-2-phenyl- and 4-amino-l-methyl-2-phenylindoles with a free β-position of the pyrrole ring with acetylacetone and dibenzoylmethane was studied. It was found that primary condensation occurs only on aminogroups and produces the corresponding enaminoketones, which under conditions of enamine acidic cyclization on the basis of dibenzoylmethane, turn into pyrrolo[2,3-h]-quinolines. The products of cyclization with participation of indole 3 atom were not detected.     

Reaction of 2,3-dimethyl-and 1,2,3-trimethyl-6-aminoindoles with ethyl 4,4,4-trifluoroacetoacetate

The comparative reactivity of 2,3-dimethyl-and 1,2,3-trimethyl-6-aminoindoles in the reaction with ethyl trifluoroacetoacetate has been studied with the aim of developing the synthesis of corresponding trifluoromethylpyrroloquinolines. Depending on the amine used, the reaction proceeds differently both at the initial stage of the formation of amides and during their transformation into trifluoropyrroloquinolines.     

Synthesis of isomeric pyrroloquinolines from 5- and 6-aminoindoles

In the case of 2,3-dimethyl-, 2-methyl-, and 2,3,6-trimethyl-5-aminoindoles, as well as 2,3-dimethyl- and 1,2,3-trimethyl-6-aminoindoles, it was shown that the enamino ketones formed in the reaction of 5- or 6-aminoindoles with 1,3-diketones undergo cyclization under the influence of acidic agents to substituted pyrroloquinolines with linear or angular ring fusion. The formation of the latter is limited by steric factors. Thus, the pronounced ortho effect of a substituent attached to the C atom (in the pyrrole ring) or 5-indolylaminovinyl ketones substantially hinders cyclization in the 4 position of the indole and promotes primary or exclusive formation of the linear isomer. Similarly, in the case of enamino ketones obtained from 6-aminoindoles, the substituent attached to the pyrrole nitrogen atom sterically hinders electrophilic attack at C₇, i.e., formation of the angular isomer.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 770–776, June, 1977.     

The potential use of 6-amino-5-methoxy(methyl)-2,3-dimethyl-and 6-amino-5-methoxy(methyl)-1,2,3-trimethyl-indoles in the synthesis of pyrrolo[2,3-f]quinolines

The reaction of 6-amino-2,3-dimethyl-and 6-amino-1,2,3-trimethyl-5-methoxy(methyl)indoles with 4,4,4-trifluoroacetoacetic ester and of 6-amino-5-methoxy-1,2,3-trimethylindole also with other β-dicarbonyl compounds has been studied. It was found that all of the amines investigated undergo condensation readily to form the corresponding enamines while the possible subsequent cyclization to give pyrrolo[2,3-f]quinolines was found only for the condensation product of 6-amino-2,3,5-trimethylindole with 4,4,4-trifluoroacetoacetic ester. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp 97–103, January, 2006.     

Reactions of acetoacetic ester with aryl- and heteroarylamines (review)

Published data on the cyclocondensation of acetoacetic ester with aryl- and heteroarylamines over the last 20 years are reviewed.     

Synthesis of heterocyclic compounds using oxaloacetic ester (review)

Published data on the use of oxaloacetic ester in the synthesis of various heterocyclic systems are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 163–187, February, 2008.     

Synthesis and antimicrobial activity of N-(indol-5-yl)trifluoroacetamides and indol-5-ylaminium trifluoroacetates substituted in the pyrrole ring

Russian Chemical Bulletin - Based on a series of 1H-indol-5-ylamines substituted in the pyrrole ring, the corresponding N-(indol-5-yl)trifluoroacetamides and indol-5-ylaminium trifluoroacetates...