SYNTHESIS AND STRUCTURE OF HYDRAZONE DERIVATIVES OF HARMINE

SYNTHESIS AND STRUCTURE OF HYDRAZONE DERIVATIVES OF HARMINE Научная публикация

Журнал

NEWS OF THE NATIONAL ACADEMY OF SCIENCES OF THE REPUBLIC OF KAZAKHSTAN-SERIES CHEMISTRY AND TECHNOLOGY
ISSN: 2224-5286 , E-ISSN: 2518-1491

Вых. Данные

Год: 2020, Номер: 3, Страницы: 88-95 Страниц : 8 DOI: 10.32014/2020.2518-1491.48

Ключевые слова

harmine; hydrazone derivative of 8-acetylharmine; N-arylidenehydrazones; H-1; C-13-NMR spectra; two-dimensional NMR spectra

Авторы

Amanzhan A. ¹ , Zhanymkhanova P.Zh ¹ , Aidanuly B. ¹ , Shults E.E. ² , Turmukhambetov A.Zh ¹ , Adekenov S.M. ¹

Организации

1	(Данные Web of science) JSC Int Res & Prod Holding Phytochem, Karaganda, Kazakhstan
2	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem SB RAS, Novosibirsk, Russia

The present paper deals with chemical synthesis based on 8-acetylharmine. It was established that interaction of 8-acetylharmine with hydrazine hydrate produces (E)-8-(1-hydrazonoethyl)-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole in a yield of 69%. It was shown, that reaction of (E)-8-(1-hydrazonoethyl)-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole with functionally substituted aromatic aldehydes (anisaldehyde, 2-fluorobenzaldehyde, 2,4-dimethoxybenzaldehyde) by boiling in methanol leads to the formation of the corresponding N-arylidenehydrazones with 56-82% yields. The structure of the synthesized compounds was characterized on the basis of one-dimensional H-1, C-13 and DEPT NMR methods, as well as data from two-dimensional COSY, HMQC, and HMBC spectra, elemental analysis and mass spectra. Correlation spectroscopic methods provided information for identification of three bond protons-protons and one bond protons-carbons correlations COSY (H-1-H-1) and HMQC (H-1.-C-13, H-1-N-15). Homo- and heteronuclear interactions, confirming the structures of new derivatives of harmine, are determined. The use of modern physicochemical and spectroscopic research methods in the present work allowed reliable and unambiguous characterization of the structure and properties of the obtained compounds.

Amanzhan A. , Zhanymkhanova P.Z. , Aidanuly B. , Shults E.E. , Turmukhambetov A.Z. , Adekenov S.M.
SYNTHESIS AND STRUCTURE OF HYDRAZONE DERIVATIVES OF HARMINE
NEWS OF THE NATIONAL ACADEMY OF SCIENCES OF THE REPUBLIC OF KAZAKHSTAN-SERIES CHEMISTRY AND TECHNOLOGY. 2020. N3. P.88-95. DOI: 10.32014/2020.2518-1491.48 WOS

Опубликована в печати:	15 июн. 2020 г.
Опубликована online:	19 июн. 2020 г.

Web of science	WOS:000541849600012
OpenAlex	W3036294376