A. S. Lyakhovnenko
North-Caucasus Federal University
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Russian Journal of Organic Chemistry | 2007
A. V. Aksenov; I. V. Borovlev; A. S. Lyakhovnenko; I. V. Aksenova
The application of compound II in the role of formylating agent is well known [2]. In the classical version the reaction is carried out without catalyst or in the presence of Lewis acids. We demonstrated that under these conditions the perimidine formylation did not occur. Therefore another combination of reagents was used as formylating agent: 3-fold excess of 1,3,5-triazine II in 80% polyphosphoric acid (PPA) at 55–60°C. The yield of aldehydes IV under these conditions was 83–91%.
Russian Journal of General Chemistry | 2007
I. V. Aksenova; A. S. Lyakhovnenko; A. V. Aksenov; I. V. Borovlev
Several methods for the synthesis of 1,3-diazapyrene derivatives have been reported previously [1 5]. However, these methods suffer from poor yields and lack of general character. In the present communication we describe a procedure that is free from the above disadvantages. The procedure is based on the vinylformylation of heterocyclic compounds, which has been developed relatively recently [6]. We have found that perimidines Ia Ic react with 3-(Nmethyl-N-phenylamino)acrolein in dichloroethane in the presence of POCl3 to give the corresponding 1,3diazapyrenes IIIa IIIc in 42 56% yields.
Chemistry of Heterocyclic Compounds | 2013
A. V. Aksenov; N. A. Aksenov; A. S. Lyakhovnenko; Alexander N. Smirnov; I. I. Levina; I. V. Aksenova
A method has been developed for the nitration of 6(7)-acylperimidines using sodium nitrite in formic acid. The reaction gives a mixture of 4(9)-, 9(4)-, and 7(6)-nitro-6(7)-acylperimidines from which the latter can be separated by extraction with chloroform. Reduction of the 6(7)-acyl-7(6)-nitro- perimidines yields 1H-1,5,7-triazacyclopenta[cd]phenalenes. Subsequent Schmidt reaction and reduction give 1,3,6,8-tetraazapyrenes.
Chemistry of Heterocyclic Compounds | 2012
A. V. Aksenov; N. A. Aksenov; A. S. Lyakhovnenko; A. B. Kumshaeva; I. V. Aksenova
Methods have been developed for the synthesis of 1,3-diazapyrenes, 8(6)-aryl-6(8)-oxo-1,6,7,8-tetra-hydro-1,3-diazapyrenes, and 1,3,7-triazapyrenes based on a three-component reaction of perimidines with 1,3,5-triazines and carbonyl compounds, benzonitrile, or vinyl butyl ether in polyphosphoric acid.
Chemistry of Heterocyclic Compounds | 2007
I. V. Aksenova; I. V. Borovlev; A. S. Lyakhovnenko; S. V. Pisarenko; A. V. Aksenov
The reaction of 1,8-diaminonaphthalene dihydrochloride with acetonitrile and butyronitrile at high temperature gave 2-methyland 2-propylperimidine respectively [1]. We investigated the reaction of 1,8-diaminonaphthalene (1) with aromatic nitriles in polyphosphoric acid* (PPA) assuming that it would form only 2-Ar-perimidines, or (by analogy with carbonic acids [2]) products of their acylation. The reaction occurred on heating the reagents above 100°C, but the unexpected products were the previously unknown 2,6,8-triaryl1,3,7-triazapyrenes 3a-c.
Chemistry of Heterocyclic Compounds | 2006
A. S. Lyakhovnenko; V. V. Trifonov; V. I. Goncharov; A. V. Aksenov
A method has been developed for the synthesis of 2,3′-biquinolines based on the reaction of β-(2-quinolyl)-2-aminostyrenes with acid amides under Vilsmeier reaction conditions.
Russian Journal of Organic Chemistry | 2013
A. S. Lyakhovnenko; T. S. Red’ko; I. V. Aksenova; N. A. Aksenov; A. V. Aksenov
_________________ 1 PPA used contained 86% of P2O5 and was synthesized by method [3]. of N1–C7a and С3–C3a bonds. We suggest such method in this report based on recently found reagents combination NaN3–polyphosphoric acid (PPA)1 [4]. The reaction of anisole (I) with NaN3 in PPA at 55–60°С within 3 h followed by the addition of phenacyl bromides IIа–IIc and subsequent heating for 4 h more at 120–130°С resulted in indoles IIIа–IIIc in 18–26%
Russian Journal of Organic Chemistry | 2013
A. V. Aksenov; N. A. Aksenov; A. S. Lyakhovnenko; I. V. Aksenova
The importance of indole derivatives as biologically active compounds is difficult to overestimate. Benzo[c,d]indoles are not an exception; for example, efficient inhibitors of thymidylate synthase were found among compounds of this series [1]. The present communication describes the synthesis of fused benzo[c,d]indole derivatives, 6H-pyrrolo[2,3,4-gh]perimidines IVa–IVc, from naphthalene-1,4,8-triamine (I) and 1,3,5-triazines IIa–IIc. We previously showed that 1,3,5-triazine in polyphosphoric acid (PPA) acts as efficient formylating and acylating agent [2–5], in particular toward naphthylamines [5]. Therefore, it may be expected that the use of 1,3,5-triazine should ensure convenient synthesis of pyrroloperimidines IVa–IVc. In fact, by heating triamine I with triazines IIa–IIc in PPA first at 80–90°C and then at 130–140°C we obtained the corresponding pyrroloperimidines IVa–IVc in 38–48% yield. The reaction is likely to involve intermediate formation of aminoperimidines IIIa–IIIc. Unlike the known procedure [6], the proposed method requires no preliminary preparation and acylation of perimidines. Furthermore, the key step in the known procedure [6] is the Schmidt reaction utilizing sodium azide in acid medium, and there exists a risk of evolution of toxic and explosive hydrazoic acid. The procedure proposed by us is free from the said disadvantage.
Russian Chemical Bulletin | 2013
A. M. Zhirov; A. S. Kolesnikova; I. V. Aksenova; A. S. Lyakhovnenko; A. V. Aksenov
Azapyrenes are used as fluorescent DNA intercalla tors1, among them are also found compounds possessing cytotoxic2 and analgesic activity.3 Nevertheless, only lim ited number of methods for the synthesis of such com pounds are known at present, and the synthesis of 1,2,6,8 tetraazapyrenes is described only in one work.4 In the present work, we suggest a method for the syn thesis of 1,2,6,8 tetraazapyrenes based on the reaction of 6(7) formyl(benzoyl)perimidines with diethyl azodicar boxylate. Lewis5—8 or Brønsted acids8,9 were used as catalysts in the reaction of azodicarboxylates with arenes. We showed that the reaction of 6(7) formyl(benzo yl)perimidines 1a—c with a two fold excess of diethyl azodicarboxylate (2) in polyphosphoric acid (PPA) at 80—90 C with subsequent treatment of the reaction mix ture with water and reflux of the solution formed led to 1,2,6,8 tetraazapyrenes 3a—c in 32—37% yields (Scheme 1). A mechanism suggested for this transformation (Scheme 2) includes the Michael addition of azo com pound 2 to perimidines 1a—c, resulting in hydrazines 5, which cyclize with the formation of dihydro derivatives of tetraazapyrenes 6. The hydrolysis and oxidation of the latter, probably, with atmospheric oxygen gives the target tetraazapyrenes 3a—c. Scheme 1
Chemistry of Heterocyclic Compounds | 2013
A. S. Lyakhovnenko; T. S. Red’ko; I. V. Aksenova; A. V. Aksenov
Polynuclear aromatic and heteroaromatic compounds with peri-annelated fiveand six-membered rings include perimidine derivatives and show a range of useful properties. The development of novel, efficient methods for preparation of such compounds is a current challenge. Although methods for preparing perimidines containing a pyrrole ring are quite numerous [1-3], there are only very limited ways for synthesizing aceperimidines [3-5]. Such methods can be based on the dinitration of acenaphthene, reduction of the nitro derivative, and subsequent cyclization using various reagents. The drawback of such methods is the large number of stages. In our work, we propose a method of synthesizing aceperimidines from the available 4-acetyland 4-benzoylacenaphthenes 1a-e, using a system of reagents developed at our laboratories [6-8]. It was found that reaction of ketones 1a-e with a fourfold excess of sodium azide in polyphosphoric acid (PPA) for 1 h at 70-80°C, followed by 4 h at 100-110°C gave the aceperimidines 3a-e in 27-46% yields.