Heterocyclization of 2-Acetylcyclopentanone

Gevorg G. Danagulyan; Данагулян Геворг Грачевич; Tigran E. Georgyan; Георгян Тигран Эдикович; Aida P. Boyakhchyan; Бояхчян Аида Пайлаковна; Anna G. Danagulyan; Данагулян Анна Геворговна

doi:10.31857/S0514749225040056

Heterocyclization of 2-Acetylcyclopentanone

Authors: Danagulyan G.G.¹^,2, Georgyan T.E.², Boyakhchyan A.P.², Danagulyan A.G.¹^,2
Affiliations:
1. Russian-Armenian University
2. Scientific Technological Center of Organic and Pharmaceutical Chemistry of the NAS of the Republic of Armenia
Issue: Vol 61, No 4 (2025)
Pages: 393-403
Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://stomuniver.ru/0514-7492/article/view/689621
DOI: https://doi.org/10.31857/S0514749225040056
EDN: https://elibrary.ru/SDIXYJ
ID: 689621

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription or Fee Access

Abstract
Full Text
About the authors
References
Supplementary files
Statistics

Abstract

Based on 2-acetylcyclopentanone, the synthesis of various heterocycles has been studied, in particular, derivatives of pyrazole, pyrimidine, condensed systems of pyrazolo[1,5-a]pyrimidine and 1,2,4-triazolo[1,5-a]pyrimidine, as well as their methyl iodides. Due to the observed nuclear Overhauser effect (NOE), in a number of cases, the structure of the synthesized substances could be proven only by using the NOESY NMR spectroscopy technique. An effective method for using NMR spectroscopy to prove the structures of the synthesized substances is proposed, by obtaining their methyl iodides and then studying the spectra of the resulting salts.

Keywords

2-acetylcyclopentanone, pyrimidine, pyrazolo[1,5-a]pyrimidine, NOESY, 1,2,4-triazolo[1,5-a]pyrimidine, alkylation

Full Text

References

Шокова Э.А., Ким Дж.К., Ковалев В.В. ЖОрХ. 2015, 51 (6), 773–847. [Shokova E.A., Kim J.K., Kovalev V.V. Russ. J. Org. Chem. 2015, 51, 755–830.] doi: 10.1134/S1070428015060019
Данагулян Г.Г., Бояхчян А.П., Туманян А.К., Киноян Ф.С., Григорян Т.А. Хим. ж. Армении. 2013, 66, 76–83.
Danagulyan G.G., Panosyan H.A., Gharibyan V.K., Hasratyan A.H. Molecules. 2023, 28 (6), 2869. doi: 10.3390/molecules28062869.
Danagulyan G.G., Arakelyan M.R., Aksenov N.A., Panosyan H.A., Ayvazyan A.G., Hasratyan A.H. J. Molec. Str. 2023, 136676 (MOLSTR_136676). doi: 10.1016/j.molstruc.2023.136676.
Ried W., Kocher E.-U. Lieb. Ann. Chem. 1961, 647 (1), 116–144. doi: 10.1002/jlac.19616470117
Петров А.А., Касаточкин А.Н., Емелина Е.Е. ЖОрХ. 2012, 48 (8), 1113–1121.[Petrov A.A., Kasatochkin A.N., Emelina E.E. Russ. J. Org. Chem. 2012, 48, 1111−1120.] doi: 10.1134/S1070428012080131
Portilla J., Quiroga J., Nogueras M., Cobo J. Tetrahedron. 2012, 68, 988–994. doi: 10.1016/j.tet.2011.12.001
Кост А.Н., Сaгитуллин Р.С., Данагулян Г.Г. ХГС. 1976, 5, 706−708.
Shaban M.A.E., Morgaan A.E.A. Adv. Heterocycl. Chem. 1999, 73, 131−177. doi: 10.1016/S0065-2725(08)60942-3
El Ashry E.S.H., Rashed N. Adv. Heterocycl. Chem. 1998, 72, 127–224. doi: 10.1016/S0065-2725(08)60316-5
Данагулян Г.Г., Саакян Л.Г., Залинян М.Г. ХГС. 1992, 2, 225–227. [Danagulyan G.G., Saakyan L.G., Zalinyan M.G. Chem. Heterocycl. Compd. 1992, 8, 186−188.]
Данагулян Г.Г., Саакян Л.Г., Паносян Г.А., Булахов Г.А., Терентьев П.Б., Залинян М.Г. ХГС, 1993, 11, 1545–1547. [Chem. Heterocycl. Compd. 1994, 5, 1332−1334.]
Danagulyan G.G., Boyakhchyan A.P., Tumanyan A.K., Danagulyan A.G., Araqelyan M.R. Chem. J. Arm. 2020, 73 (4), 349–358. http://chemjournal.sci.am; https://arar.sci.am/publication/287795
Danagulyan G.G., Ostrovskii V.A., Gharibyan V.K. ЖОрХ, 2022, 58 (11), 1229–1233. [Russ. J. Org. Chem. 2022, 58, 1648–1651.] doi: 10.1134/S1070428022110136