Laboratory of Amines and Aminium Compounds

Head of the Laboratory

 

Varduhi Suren Hovsepyan, PhD in Chemistry, Associate Professor

Telephone

(+374) 10 241-540

(+374) 94 936-780

E-mail: hovsepyanvarduhi.chem@gmail.com

History of the Laboratory of Amines and Ammonium Compounds

In 1957, the Laboratory of Amino Compounds was founded by Araksi Babayan, who led it until 1991. Through her scientific and educational efforts, a prominent school of chemists was established in Armenia, many of whom continued to advance the field of organic chemistry in both research and academic directions.

Over the years, the laboratory has functioned in the form of parallel research labs and research groups, including:

  • Laboratory of Amino Compounds – Sasun Kocharyan (1992–2006)
  • Laboratory of Nitrogen-Containing Organic Compounds – Ara Gyulnazaryan (2008–2022)
  • Laboratory of Amino Compounds – Emma Chukhajyan (2008–2024)
  • Group of Nitrogen-Containing Organic Compounds – Varduhi Hovsepyan (2024–2025)

In 2025, based on the foundation of these laboratories and research groups, a new scientific unit was established – the Laboratory of Amines and Ammonium Compounds.

Current activity

The laboratory currently has 12 members, of which

3 PhD 

1 applicant

3 junior researchers

3 master’s students

2 laboratory assistants

Scientific achievements

The founder of the Laboratory of Amino Compounds and one of the pioneers of organic chemistry in Armenia, Araksi Babayan, researched the synthesis of acetylenic glycols and alkylation reactions of compounds with diverse structures in the presence of quaternary ammonium salts. She discovered several reactions involving ammonium salts, including dehydrochlorination–cleavage, rearrangement–cleavage, rearrangement–cyclization, and cyclization–cleavage reactions.

Extensive research has been conducted in the laboratory on the rearrangement reactions of quaternary ammonium salts (QAS), with a particular focus on the Stevens and Sommelet rearrangements, as well as hydride shift, halogenation, dehydrohalogenation, and base-catalyzed intramolecular cyclization and recyclization reactions.

 

Scientific results

  • More than 800 scientific papers have been published
  • More than 6 dozen candidate and doctoral theses were defended.

 

Scientific Focus of the Laboratory

The main research directions of the Laboratory of Amines and Ammonium Compounds are:

Sigmatropic rearrangements of quaternary ammonium salts (QAS)

Bromination reactions of QAS

Synthesis of mono-, bis-, tris-, multi-, and polyammonium salts

Modification of chitosan with QAS

Modification of Armenian bentonite with QAS

Cyclization and recyclization reactions of QAS

Currently, the laboratory is engaged in the functionalization of QAS, targeted synthesis of amines and QAS, and SAR studies, aiming to obtain unsaturated compounds with antimicrobial and anticorrosion properties, as well as potential bioactive isoindolinium and dihydroisoindolinium salts, and p-terphenyl and its derivatives.

List of scientific publications published in the last 5 years

    1. Hovsepyan V. S., Babakhanyan A. V., Balyan K. V., Harutyunyan N. A, Khamisyan Sh. G., Hobosyan N. G., Sargsyan H. B. // Synthesis and antimicrobial properties of quaternary ammonium salts with two propargyl groups. Russian Journal of General Chemistry, 2024, Vol. 94, No. 7, pp. 1603–1609.
    2. Khallouf R., Zaqaryan N., Ohanyan A., Chailyan S., Danielyan K., Hovsepyan V. // Newly synthesized HV-12 prevents aggregation of the platelets via P2Y12. // Free Radical Biology and Medicine. 2024 Volume 224, Supplement 1, 2024, P. S58
    3. Varduhi Suren Hovsepyan, Gohar Mkrtich Arajyan, Abdulwahabb Al-Chachani, Gohar Khristafor Musheghyan, John Sarkissian, Ivan Georgi Gabrielyan. // Georgian Medical News. 2025․ The ratio of excitatory and inhibitory synaptic processes in neurons of the еntorhinal cortex of the brain, activated by basolateral amygdala on the model of Parkinson’s disease, under conditions of protection by hydrocortisone. 2024․ Vol. 356 No. 11. P. 50-58
    4. Musheghyan, G.Kh., Arajyan, G.M., Poghosyan, M.V., Hovsepyan, V.S., Sarkissian, J.S. Synaptic processes in the antinociceptive somatosensory cortex of the brain are activated by the ventral posterior-lateral thalamic nucleus in a rotenone model of Parkinson’s disease. Georgian Medical News, 2023, 336(3), pp. 117–122
    5. Hovsepyan V.S., Safaryan G.G., Stepanyan H.M., Muradyan R.Y., Balyan K.V., Sargsyan H.B., Hobosyan N.G., Babakhanyan A.V. Synthesis and antimicrobial activity of quaternary ammonium salts containing unsaturated groups with alkyl or alkyl oxycarbonyl methyl groups. New Trends in Chemistry 2023 175
    6. Овсепян В. С., Бабаханян А. В. Сигматропная перегруппировка аммониевых солей, содержащих 4-алкилоксибутин-2-ильную группу / ученые записки армянского государственного педагогического университета им. Х. Абовяна / №1 (36) 2019 с.29-32
    7. Гюльназарян А.Х.Г., Саакян Т.А., Еремян А.Б., Мурадян Г. М., Пароникян Р.Б., Степанян Г.М., / Антимикробная активность аммониевых солей, содержащих 2,3- дибромалкенильную группу. Ученые записки Арм. Пед. Университета им.  Х.Абовяна Естесв. Науки, №1(36) ,2019, с. 24-28
    8. Саакян Т.А., Гюльназарян А.Х.,  Мурадян  Г.М., Еремян А.Б., Паносян Г.,А., /Ацетальный гидролиз при бромировании аммониевой  соли с пропаргильной и диоксолановой  группировкой. Материалы VI научной конф. Армянского хим. общества “Вызовы 21-ого века”, Ереван, 7-11 окт. 2019г. с.11
    9. Гюльназарян А. Х.,  Саакян Т., А., Саргсян Г.,Т., Еремян А., Б.,  / 3,4-Бис-(дибромметил) 1,1- диметил-2,5 дигидро-1 н-пирол-1-иум бромид  кристаллогидрат.   Сборник “Синтезы гетероциклических соединений” Выпуск 19, Ереван 2020г., с.91-62.
    10. Гюльназарян А.Х., Саакян Т., А., Еремян А.,Б.,  Айвазян А., Б., /Синтез и бромирование  аммониевых солей, содержащих  две аллилные  группы.   Химический   журнал Армении 75, №2, 2022
    11. Саакян  Т., А., Еремян А.,Б., /Дезалкилирование  при галодировании метил-N, N, N-трипропин -2-иламмоний бромида.  New emerging   trends in chemistry conference (Newtrendschem-2023, Yerevan, Armenia, September 24-28, 2023
    12. Гюльназарян А.Х., Саргсян Г.Т., Аветикян М.Н. Перегруппировка Стивенса аммониевых солей, содержащих две бут-2-инильные группы. // Хим. ж. Арм. т. 73, №1-2, с.69, 2020.
    13. Гюльназарян А.Х., Саакян Т.А., Саргсян Г.Т., Еремян А.Б. 3,4-Бис-(дибромметил)-1,1-диметил-2,5-дигидро-1н-пиррол-1-иум бромид кристаллогидрат. Сборник “Синтезы гетероциклических соединений“ Выпуск 19, Ереван, 2020 г.с.61-62.
    14. Саргсян Г. T., Саакян Т.А., Гюльназарян А.Х., Бабаханян А.В. // Перегруппировка Стивенса аммониевых солей, содержащих две бут-2-инильные группы. Материалы VI научной конф. Армянского хим. общества “Вызовы 21-ого века”, Ереван, 7-11 окт. 2019. с.116.
    15. Chukhajian, E. O., Ayrapetyan, L. V., Shahkhatuni, K. G., Chukhajian, E. O., Mkrtchyan, H. S., & Panosyan, H. A. – Base-Catalyzed Intramolecular [4+2]-Cycloaddition of [3-Arylprop-2-yn-1-yl] (3-phenylprop-2-en-1-yl) ammonium Bromides and Cleavage of the Cycloaddition Products in Aqueous Alkali // Russian Journal of Organic Chemistry, 2019, 55, 319–324
    16. Chukhajian, E. O., Ayrapetyan, L. V., Mkrtchyan, H. S., Chukhajian, E. O., & Panosyan, H. A. -Synthesis of 6-Bromo-3a,4-dihydrobenzo[f]isoindolinium Bromides and Their Aqueous-Alkaline Cleavage // Russian Journal of Organic Chemistry, 2019, 55, 1124-1130
    17. E. O. Chukhajian, H. R. Gevorgyan, K. G. Shahkhatuni, El. O. Chukhajian, H. A. Panosyan // Base-Catalyzed Intramolecular Cycloaddition of Dialkyl(4-hydroxybut-2-yn-1-yl) [3-(4-bromophenyl) prop-2-yn-1-yl] ammonuim Chlorides and Recyclization of the Products / Russian Journal of Organic Chemistry, 2019, 55 (4), 473-478.
    18. Chukhajian E.O., Shahkhatuni K.G., Gevorgyan H.R., Khachatryan A. A. Synthesis of derivatives of 4-hydroxymethylisoindolinium chlorides and their intramolecular recyclization. 4th Edition of International Conference on Catalysis and Green Chemistry, May 13-14, 2019 – Tokyo, Japan, Book of abstracts, p.105-106.
    19. E. O. Chukhajian, L. V. Ayrapetyan, H. S. Mkrtchyan & H. A. Panosyan-Synthesis of Mixed Secondary and Tertiary Amines // Russian Journal of Organic Chemistry, 2020, 56, 353-355
    20. E. H. Chukhajian, L. V. Ayrapetyan, K. G. Shahkhatuni & El. H. Chukhajian – Synthesis of 4-Bromo-1,1′:4′,1″-terphenyl and 4-Methyl-1,1′:4′,1″-terphenyl. // Russian Journal of Organic Chemistry, 2020, 56, 1738-1743
    21. E. O. Chukhajian, L. V. Ayrapetyan, K. G. Shahkhatuni, H. S. Mkrtchyan & H. A. Panosyan – Intramolecular Cycloaddition of [3-(Naphthalen-1-yl) prop-2-yn-1-yl] (3-phenylprop-2-en-1-yl) ammonium Bromides and Cleavage of Some of the Obtained Cyclic Salts in Aqueous Alkali // Russian Journal of Organic Chemistry, 2020, 56, 2087-2091
    22. E. O. Chukhajian, L. V. Ayrapetyan, and G. A. Panosyan – Synthesis of 1-[(1,1´-biphenyl)-4-yl] naphthalene from amines obtained by the Stevens rearrangement of N-[3-(naphthalen-1-yl) prop-2-yn-1-yl]-3-phenylprop-2-en-1-aminium bromides // Russian Chemical Bulletin, 2022, 71, 1262-1265
    23. E. O. Chukhadzhyan, L. V. Ayrapetyan, H. S. Mkrtchyan, A. K. Aloyan & H. A. Panosyan – Spiro 1-Allyl-4-phenyl-3a,4-dihydrobenzo[f]isoindolininum Derivatives by Base-catalyzed Intramolecular Cyclization // Russian Journal of Organic Chemistry, 2023, 59, 834-839
    24. Chukhadzyan, E.O., Ayrapetyan, L.V. New Method for the Synthesis of Terphenyl and Its Derivatives // Russian Journal of Organic Chemistry, 2023, 59, 1730–1738
    25. H.R. Gevorgyan, E.O. Chukhajian // Rearrangment–Cyclization of Dialkyl(4-hydroxybut-2-ynyl) (3-phenylprop-2-enyl) ammonium Bromides in the Presence of Aqueous Alkali. / Russian Journal of Organic Chemistry, 2024, 60, 806–810.
    26. H. R. Gevorgyan, E. O. Chukhadzhyan, and L. V. Ayrapetyan – Mechanism of Intramolecular Cyclization of Quaternary Ammonium Salts Containing a β,γ-Unsaturated Fragment and Various π4 Fragments // Russian Journal of Organic Chemistry, 2024, 60, 984–994