Synthesis, molecular and crystalline structure of 8-formylharmine

Synthesis, molecular and crystalline structure of 8-formylharmine Full article

Journal

Bulletin of the University of Karaganda-Chemistry
ISSN: 2518-718X , E-ISSN: 2663-4872

Output data

Year: 2020, Number: 100, Pages: 45-51 Pages count : 7 DOI: 10.31489/2020Ch4/45-51

Tags

NMR spectroscopy; mass- spectrometry; X-ray diffraction analysis; crystal structure; hydrogen bond; harmine; 8-formylharmine; harmine derivatives

Authors

Turdybekov K.M. ¹ , Nurmaganbetov Z.H.S. ² , Turdybekov D.M. ³ , Mukusheva G.K. ¹ , Gatilov Yu. ⁴

Affiliations

1	(Данные Web of science) Karagandy Univ, Univ St 28, Karaganda, Kazakhstan
2	(Данные Web of science) Karaganda Med Univ, Gogol St 40, Karaganda 100000, Kazakhstan
3	(Данные Web of science) Karaganda State Tech Univ, Dept Phys, N Nazarbaev St 56, Karaganda 100010, Kazakhstan
4	(Данные Web of science) NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk, Russia

For the first time, synthesis of 8-formylharmine by the Vilsmeier reaction was carried out. 8-Formylharmine was obtained by treating alkaloid harmine with dichloromethoxymethane in the presence of SnCl4. The yield of the target product was 64 %. The structure of the obtained compound was established on the basis of H-1 and C-13 NMR spectroscopy as well as mass-spectrometry data. The crystalline structure of 8-formylharmine was determined by X-ray diffraction. It has been shown that the replacement of the hydrogen atom in the harmine molecule with a formyl group occurs at the C8 atom. It was revealed that the methoxy group at the C7 atom changes its orientation to the opposite one as compared to the orientation in the harmine molecule and its salts due to the mutual Van der Waals repulsion of the methoxy and formyl groups. A weak intramolecular hydrogen bond was found in the crystal between the O2 atom of the formyl group and the hydrogen atom of the secondary amino group. It was shown that molecules in the crystal form an intermolecular hydrogen bond between the same atoms (O2 and HN9A), as a result of which dimers are formed.

Turdybekov K.M. , Nurmaganbetov Z.H.S. , Turdybekov D.M. , Mukusheva G.K. , Gatilov Y.
Synthesis, molecular and crystalline structure of 8-formylharmine

Bulletin of the University of Karaganda-Chemistry. 2020. N100. P.45-51. DOI: 10.31489/2020Ch4/45-51 WOS РИНЦ

Full text from publisher

Published print:	Dec 30, 2020
Published online:	Dec 30, 2020

Web of science	WOS:000604536400004
Elibrary	44860026
OpenAlex	W3118818323