Home / Publications / New 1-hetarylfuropyridines and chromenes based on pyridoxal and 4-hydroxycoumarin

New 1-hetarylfuropyridines and chromenes based on pyridoxal and 4-hydroxycoumarin

Alexey Vladimirovich Trifonov 1
Alexey Vladimirovich Trifonov
Ludmila Konstantinovna Kibardina 1
Ludmila Konstantinovna Kibardina
Alexey Borisovich Dobrynin 1
Alexey Borisovich Dobrynin
Amirjon A Ali Akhunov 2
Amirjon A Ali Akhunov
Michael Arkad'evich Pudovik 1
Michael Arkad'evich Pudovik
Alexander Romanovich Burilov 1
Alexander Romanovich Burilov
Published 2020-11-03
CommunicationVolume 30, Issue 6, 765-767
3
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Trifonov A. V. et al. New 1-hetarylfuropyridines and chromenes based on pyridoxal and 4-hydroxycoumarin // Mendeleev Communications. 2020. Vol. 30. No. 6. pp. 765-767.
GOST all authors (up to 50) Copy
Trifonov A. V., Kibardina L. K., Dobrynin A. B., Ali Akhunov A. A., Pudovik M. A., Burilov A. R. New 1-hetarylfuropyridines and chromenes based on pyridoxal and 4-hydroxycoumarin // Mendeleev Communications. 2020. Vol. 30. No. 6. pp. 765-767.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2020.11.025
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.11.025
TI - New 1-hetarylfuropyridines and chromenes based on pyridoxal and 4-hydroxycoumarin
T2 - Mendeleev Communications
AU - Trifonov, Alexey Vladimirovich
AU - Kibardina, Ludmila Konstantinovna
AU - Dobrynin, Alexey Borisovich
AU - Ali Akhunov, Amirjon A
AU - Pudovik, Michael Arkad'evich
AU - Burilov, Alexander Romanovich
PY - 2020
DA - 2020/11/03
PB - Mendeleev Communications
SP - 765-767
IS - 6
VL - 30
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Trifonov,
author = {Alexey Vladimirovich Trifonov and Ludmila Konstantinovna Kibardina and Alexey Borisovich Dobrynin and Amirjon A Ali Akhunov and Michael Arkad'evich Pudovik and Alexander Romanovich Burilov},
title = {New 1-hetarylfuropyridines and chromenes based on pyridoxal and 4-hydroxycoumarin},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.11.025},
number = {6},
pages = {765--767},
doi = {10.1016/j.mencom.2020.11.025}
}
MLA
Cite this
MLA Copy
Trifonov, Alexey Vladimirovich, et al. “New 1-hetarylfuropyridines and chromenes based on pyridoxal and 4-hydroxycoumarin.” Mendeleev Communications, vol. 30, no. 6, Nov. 2020, pp. 765-767. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.11.025.

Keywords

chromenes.
chromeno[3′,4′:5,6]pyrano[2,3-c]pyridines
electrophilic substitution
furo[3,4-c]pyridines
heterocyclization
pyridoxal

Abstract

Pyridoxal in the absence of catalyst forms furo[3,4-c]pyridine species (ortho aldehyde and hydroxymethyl groups are involved) which is further transformed into C–C hybrid with 4-hydroxycoumarin. Different products of chromeno-[3′,4′:5,6]pyrano[2,3-c]pyridine type are formed when pyridoxal hydrochloride or more sophisticated 2,4-dihydroxybenzaldehyde derivative are applied (herein, ortho aldehyde and hydroxy groups are involved into heterocyclization).

References

1.
Hybrid Compounds
Müller-Schiffmann A., Sticht H., Korth C.
BioDrugs, 2012
2.
Benzofuroxan and Furoxan. Chemistry and Biology
Cerecetto H., González M.
Topics in Heterocyclic Chemistry, 2007
4.
Pyridoxal: A New Alkylating Agent in Reactions with Phenols and Polyphenols
Kibardina L.K., Trifonov A.V., Burilov A.R., Gazizov A.S., Pudovik M.A.
Russian Journal of General Chemistry, 2018
5.
Kibardina L.K., Trifonov A.V., Dobrynin A.B., Pudovik M.A., Burilov A.R.
Mendeleev Communications, 2018
6.
New Furopyridines Containing Pyridoxal and Pyrazolone Fragments
Kibardina L.K., Trifonov A.V., Burilov A.R., Pudovik M.A.
Russian Journal of General Chemistry, 2018
7.
Antihuman Immunodeficiency Virus Type 1 (HIV-1) Activity of Rare Earth Metal Complexes of 4-Hydroxycoumarins in Cell Culture
Manolov I., Raleva S., Genova P., Savov A., Froloshka L., Dundarova D., Argirova R.
Bioinorganic Chemistry and Applications, 2006
8.
Synthesis and Anticoagulant Activities of Substituted 2,4-Diketochromans, Biscoumarins, and Chromanocoumarins
9.
Biscoumarin: new class of urease inhibitors; economical synthesis and activity
Khan K.M., Iqbal S., Lodhi M.A., Maharvi G.M., Ullah Z., Choudhary M.I., Rahman A., Perveen S.
Bioorganic and Medicinal Chemistry, 2004
12.
First-generation agents: aspirin, heparin and coumarins
Mueller R.L.
Best Practice and Research in Clinical Haematology, 2004
13.
Ring opening reactions of nitrogen heterocycles
Smolobochkin A.V., Gazizov A.S., Burilov A.R., Pudovik M.A., Sinyashin O.G.
Russian Chemical Reviews, 2019
19.
KHODABAKHSHI S., KARAMI B., ESKANDARI K., RASHIDI A.
South African Journal of Chemistry, 2015
21.
Synthesis and Urease Enzyme Inhibitory Effects of Some Dicoumarols
Khan K.M., Iqbal S., Lodhi M.A., Maharvi G.M., Perveen S., Choudhary M.I., Atta-ur-Rahman, Chohan Z.H., Supuran C.T.
Journal of Enzyme Inhibition and Medicinal Chemistry, 2004
22.
Synthesis of Biscoumarin and Dihydropyran Derivatives and Evaluation of Their Antibacterial Activity
Li J., Lv C., Li X., Qu D., Hou Z., Jia M., Luo X., Li X., Li M.
Molecules, 2015
23.
APEX2 (Version 2.1), SAINTPlus, Data Reduction and Correction Program (Version 7.31A), Bruker Advanced X-ray Solutions, Bruker AXS, Madison, Wisconsin, USA, 2006.
24.
G. M. Sheldrick, SADABS, Program for Empirical X-ray Absorption Correction, Bruker-Nonius, 1990-2004.
25.
10.1016/j.mencom.2020.11.025_bib0125
Sheldrick
Acta Crystallogr., 2015
26.
WinGXsuite for small-molecule single-crystal crystallography
Farrugia L.J.
Journal of Applied Crystallography, 1999
27.
10.1016/j.mencom.2020.11.025_bib0135
Spek
Acta Crystallogr., 2009
28.
Mercury CSD 2.0– new features for the visualization and investigation of crystal structures
Macrae C.F., Bruno I.J., Chisholm J.A., Edgington P.R., McCabe P., Pidcock E., Rodriguez-Monge L., Taylor R., van de Streek J., Wood P.A.
Journal of Applied Crystallography, 2008