Laboratory of Nitrogen Heterocycles

Head of the laboratory Gevorg Grach Danagulyan, Corresponding Member of the National Academy of Sciences of the Republic of Armenia, Doctor of Chemical Sciences, Professor Orcid.org/0000-0002-3591-4529 Phone: (+37410) 287-330 (+37494) 544-955 Email:gdanag@email.com       The laboratory’s main research areas are: Chemistry of nitrogen-containing heterocycles, investigation of new nucleophilic recyclizations of pyrimidines, and the synthesis of biologically active substances.

1. a) Conversion of pyrimidinium salts to pyridine derivatives under the action of various amines (the so-called “rearrangement with transamination”);
2. b) An unusual rearrangement of 1,2-dialkylpyrimidinium iodides into pyrazolo[1,5-a]pyrimidine derivatives, occurring under the action of carboxylic acid hydrazides, due to the opening of the pyrimidine ring and the incorporation of a reagent fragment into the reaction product;
3. c) Recyclization of 1,2-dialkylpyrimidinium iodides into 1,2,4-triazole derivatives, occurring under the action of monosubstituted hydrazines;
4. d) C-C recyclization of pyrimidines, including “double C-C recyclization” of substituted 6-acetyl-7-hydroxypyrazolo[1,5-a]pyrimidines to 7-methylpyrazolo[1,5-a]pyrimidines.
5. e) Study of selective major isotope H/D exchange in pyrimidines;
6. f) Finding relationships between the structure of nitrogen heterocycles and their biological activity.

The laboratory has collaborated and continues to collaborate with a number of leading scientists worldwide. The head of the laboratory has held joint research grants with such scientists as Professor Alan R. Katritzky (University of Florida, USA), Professor A. Namor (England), David A. Gewirtz (Virginia University, USA), Academician of the Russian Academy of Sciences O.N. Chupakhin, Academician of the Russian Academy of Sciences V.N. Charushin, Professor V.A. Ostrovsky, and Corresponding Member of the Russian Academy of Sciences V.L. Rusinov.   History of the Laboratory of Nitrogen Heterocycles The laboratory was founded by G. Danagulyan in 2001 at the Institute of Organic Chemistry of the National Academy of Sciences of the Republic of Armenia. Current Activities The laboratory employs one doctor of science, two candidates of chemical sciences, and four certified specialists.   Best results  

• Study of recyclizations of 1,2-dialkylpyrimidinium salts under the action of various nucleophiles (amines, hydrazines, hydrazides, aminoazoles, C-nucleophiles).

• A general ideology of nucleophilic recyclizations of pyrimidines under the action of nucleophiles is proposed.

• An efficient method has been developed for introducing deuterium atoms into methyl groups located in the azine fragment of both pyrimidines and azolo[1,5-a]pyrimidines

Danagulyan G. G., Panosyan H. A., Gharibyan V. K., Hasratyan A. H. // Molecules, 2023, v. 28, 2869, https://doi.org/10.3390/molecules28062869 Danagulyan G.G., Arakelyan M.R., Aksenov N.A., Panosyan H.A., Ayvazyan A.G., Hasratyan A.H. // J. Molecul. Str., 2024, 1295 136676. doi.org/10.1016/j.molstruc.2023.136676.

• Danagulyan G. G., Panosyan H. A., Gharibyan V. K., Hasratyan A. H. // Molecules, 2023, v. 28, 2869, https://doi.org/10.3390/molecules28062869Danagulyan G.G., Arakelyan M.R., Aksenov N.A., Panosyan H.A., Ayvazyan A.G., Hasratyan A.H. // J. Molecul. Str., 2024, 1295 136676. doi.org/10.1016/j.molstruc.2023.136676.
  • «Rearrangement with transamination» is a tool for the targeted construction of pyridines (nicotinic acid derivatives) with various amino-containing groups, including fragments of natural substances.

• Recyclization of 1,2-dialkylpyrimidinium salts under the action of hydrazines

Danagulyan G.G.,  Panosyan G.A. and  Sahakyan L.G. //Chemistry of Heterocyclic Compounds, 2007, v. 43, N 8, p. 996-1000. Danagulyan, G.G., Khachatryan, L.S., Danagulyan, А.G., Dangyan M.Yu., Panogyan H.A. // Russ J. Org. Chem. v. 61, 6, p. 974–980 (2025). doi.org/10.1134/S1234567825601469 A.R.Katritzky– G.G.Danagulyan: Award NFSAT-US CRDF CH 090 02/BGP 12040 “Introduction of pharmacophore groups into biogenic pyridines by pyrimidine-recyclizations”

• Պիրիմիդինների С-С-ռեցիկլում

Vardanyan R.S., Hruby V.J., Danagulyan G.G., Mkrtchyan A.D. // J. Heterocyclic Chemistry, v. 42, N 5, p.557–562 (2005). Danagulyan G.G., Mkrtchyan A.D., Panosyan G.A.//Chemistry of Heterocyclic Compounds, v. 41, N 4, p.485–491 (2005). Vardanyan R.S., Hruby V.J., Danagulyan G.G., Mkrtchyan A.D. // Heterocyclic Comm., v. 17, p.129–133 (2011).

• Recyclization of 1,2-dialkylpyrimidinium salts under the action of carboxylic acid hydrazides. A new route to the synthesis of pyrazolo[1,5-a]pyrimidines

G.G. Danagulyan, D.A. Tadevosyan, R.A. Tamazyan, G.A. Panosyan// Chemistry of Heterocyclic Compounds, 2006, v. 42, N 2, P. 233-245 G.G. Danagulyan, A.K. Tumanyan, O.S. Attaryan, R.A. Tamazyan, A.G. Danagulyan, A.G. Ayvazyan. // Chemistry of Heterocyclic Compounds, 51, 483-490 (2015). Award 13RF-087 “Transformations of π-deficient heterocycles under the action of nucleophilic reagents”. G.G. Danagulyan, together with Academician of the Russian Academy of Sciences O.N. Chupakhin (Ural Federal University, Yekaterinburg). Danagulyan, G.G., Khachatryan, L.S., Danagulyan, А.G., Dangyan M.Yu., Panogyan H.A. // Russ J. Org. Chem. v. 61, 6, p. 974–980 (2025). doi.org/10.1134/S1234567825601469

• Identifying relationships between the structure of nitrogen heterocycles and their biological activity.

    Azolopyrimidines exhibiting high activity against breast and colorectal cancer. Azolopyrimidines exhibiting high antifungal activity.                               Pyrimidine derivatives active against type II diabetes       V.А. Ostrovskii, G.G. Danagulyan, O.M. Nesterova, Y.N. Pavlyukova, V.V. Tolstyakov, O.S. Zarubina, P.А. Slepukhin, Y.L. Esaulkova, A.А. Muryleva, V.V. Zarubaev, R.E. Trifonov // Chemistry of Heterocyclic Compounds 2021, 57(4), 448–454. doi: 10.1007/s10593-021-02922-6. Epub 2021 May 14. https://pubmed.ncbi.nlm.nih.gov/34007083/.