Azaindole derivatives

1-Benzyl-6-hydroxy-7-cyano-5-azaindoline, which was converted to 6-chloro-5-azaindoline through 6-hydroxy-5-azaindoline, was synthesized from O-methylbutyrolactim through 1-benzyl-2-pyrrolidone, 1-benzyl-2-cyano (carbamoylmethylene)-pyrrolidine, and the product of its condensation with dimethylformamide diethylacetal.See [1] for communication LII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 355–358, March, 1978.     

Lactam and acid amide acetals. 64. Acylation of enamino ketones of the indolin-3-one and 2-pyrrolin-4-one series and synthesis of 2-indolyl- and 5-pyrrolylacrylic acid derivatives

The reaction of 2-(N,N-dimethylaminomethylene)indolin-3-one and 2-methyl-3-ethoxycarbonyl-5-(N,N-dimethyl aminomethylene)-2-pyrrolin-4-one with acyl halides was used to synthesize immonium salts, the aqueous hydrolysis of which leads to 2-formyl-3-hydroxyindole and 4-hydroxy-5 formylpyrrole derivatives. -Cyano--(2-indolyl)- and -cyano--(5-pyrrolyl)acrylic acid derivatives were synthesized by reaction of immonium salts of the pyrrole series, 4 acyloxy-5-formylpyrrole and 2-formyl-3-acyloxyindole derivatives, with compounds that contain an active methylene group.See [1] for Communication 63.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 343–348, March, 1991.     

Acetals of lactams and acid amides. 67. Polarographic behavior of enamines of the indoles series in anhydrous DMF

The polarographic behavior of derivatives of 2-aminomethyleneindoxyl and 3-aminomethyleneoxindole in anhydrous DMF has been studied and the results compared with data on the polarographic reduction of substituted aminomethyleneacetophenones and of related enaminoketones and eneaminoamides. It is established that the ease of reduction is determined by the nature of the substituent on the enamine and indole nitrogen atoms and also by the presence or absence of an -methyl group in the -position of the eneamines (for noncyclic enaminoketones).For Communication 66, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 642–648, May, 1991.     

Synthesis and ionization constants of N-(4-carbethoxy-5-pyrazolyl)amidines

A number of N-(4-carbethoxy-5-pyrazolyl) amidines were synthesized by the reaction of acetals of amides and lactams with 4-carbethoxy-5-aminopyrazole, and their ionization constants in 50% alcohol were measured. It is shown that the increased basicities of the amidines obtained from the lactam acetals and dimethylacetamide acetal as compared with the basicity of N-(4-carbethoxy-5-pyrazolyl)-N,N-dimethylformamidine are due to the smaller degree of steric hindrance to conjugation in the latter.Communication XXIV from the series Acetals of lactams and acid amides. See [1] for communication XXIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 379–381, March, 1978.     

Reaction of Naphtho- and Benzimidazolequinones with Enamines. Synthesis of Condensed Benzofurans and Indoles

The reaction of naphthoquinone with nitroenamines and the interaction of benzimidazolequinones with derivatives of -aminocrotonic ester have been studied. It was shown that in the first case only the synthesis of naphthofurans occurs but in the second imidazoindoles are formed.     

Heterocyclic Quinones in ihe Nenitzescu Reaction. Synthesis of Furo- And Pyrroloquinolines from 2-Methoxycarbonyl-4-oxo-5,8-quinolinequinone

Derivatives of furo[2,3-f]quinoline were synthesized by the reaction of the enamines of acetylacetone and benzoylacetone with 2-methoxycarbonyl-4-oxo-5,8-quinolinequinone. A derivative of pyrrolo[2,3-h]quinoline was obtained from N-benzyl--aminocrotonic ester.     

New approach to the synthesis of 4-amino-2-pyridone and 1-phenyl-1,6-naphthyridinone derivatives based on substituted 3-and 5-formyl-2-pyridones

The reactions of 3-cyano-3(5)-formyl-2-oxo-4-(phenylamino)-1,2-dihydropyridines with CH acids were studied. The previously unknown fused 2-pyridone derivatives containing the 4-aminopyridine fragment were synthesized by the Knoevenagel reaction. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1416-1420, August, 2006.     

Comparison of reactivities of 1- and 4-oxotetrahydrocarbazoles in reactions with nucleophilic and electrophilic reagents

The half-wave potentials of polarographic reduction of the carbonyl group in unsubstituted and N-methyl- and N-phenylsulfonyl-substituted 1- and 4-oxotetrahydrocarbazoles and their reactivities in reactions with nucleophilic (NaBH₄, malonodinitrile, and cyanoacetamide) and electrophilic (DMF dimethyl acetal) reagents were compared. 4-Oxotetrahydrocarbazoles are much less reactive than 1-oxotetrahydrocarbazoles. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1832–1836, August, 2005.     

The aza-Nenitzescu reaction. Synthesis of indazole derivatives by condensation of quinones with hydrazones

In a continuation of the study of the aza-Nenitzescu reaction new derivatives of 5-hydroxyindazole, 4,7-dioxoindazole, and 4,9-dioxobenzindazole have been obtained from the reaction of p-benzoquinone and naphthoquinone with substituted hydrazones. “NIOPIK” State Scientific Center of the Russian Federation, Moscow 103787, Russia; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 640–644, May 1999.