Reactions of pyridoxal derivatives with phosphorus P(IV) acid chlorides

Article abstract of DOI:10.1080/10426507.2018.1539846

Interaction of cyclic derivatives of pyridoxal (1-ethoxy- and 1-diethylaminofuropyridines) with chlorides of phosphoric and carboxylic acids is carried out with the participation of phenolic hydroxyl pyridoxal. Depending on the reaction conditions in the case of aminofuropyridine, the formation of phosphorylated aminofuropyridines and hydroxyfuropyridines is possible.

Full text of DOI:10.1080/10426507.2018.1539846

Phosphorus, Sulfur, and Silicon and the Related Elements
ISSN: 1042-6507 (Print) 1563-5325 (Online) Journal homepage: http://www.tandfonline.com/loi/gpss20
Reactions of pyridoxal derivatives with
phosphorus P(IV) acid chlorides
Lyudmila K. Kibardina, Roza Kh. Bagautdinova, Alexey V. Trifonov, Michael A.
Pudovik & Alexander R. Burilov
To cite this article: Lyudmila K. Kibardina, Roza Kh. Bagautdinova, Alexey V. Trifonov, Michael A.
Pudovik & Alexander R. Burilov (2018): Reactions of pyridoxal derivatives with phosphorus P(IV)
acid chlorides, Phosphorus, Sulfur, and Silicon and the Related Elements
To link to this article: https://doi.org/10.1080/10426507.2018.1539846
Published online: 18 Nov 2018.
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PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS
https://doi.org/10.1080/10426507.2018.1539846
Reactions of pyridoxal derivatives with phosphorus P(IV) acid chlorides
Lyudmila K. Kibardina , Roza Kh. Bagautdinova , Alexey V. Trifonov , Michael A. Pudovik, and
Alexander R. Burilov
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, Kazan, Russia
ABSTRACT
ARTICLE HISTORY
Received 24 September 2018
Accepted 19 October 2018
Interaction of cyclic derivatives of pyridoxal (1-ethoxy- and 1-diethylaminofuropyridines) with
chlorides of phosphoric and carboxylic acids is carried out with the participation of phenolic hydroxyl
pyridoxal. Depending on the reaction conditions in the case of aminofuropyridine, the formation of
phosphorylated aminofuropyridines and hydroxyfuropyridines is possible.
KEYWORDS
Pyridoxal; aminofuropyridine;
phosphorylation
GRAPHICAL ABSTRACT
1. Results and discussion
compounds can be obtained. It has been found that the
interaction of equimolar amounts of 1-diethylaminofuropyri-
dine 1a or 1-ethoxyfuropyridine 1b with phosphorus P(IV)
acids tiochlorides 2a,b, produces products 3a–c or 3a and 4
depending on the reaction conditions (Scheme 1).
Earlier we have showed that pyridoxal, which is a polyfunc-
tional compound, is a convenient synthetic platform for
obtaining new types of linear and cyclic structures.
Reactions of pyridoxal derivatives with inorganic, organic,
phosphorus acids allows the preparation of salt structures with
the participation of a pyridinium nitrogen atom.[1–3] With the
participation of the aldehyde group, new azomethines and
imidazolidines were synthesized.[4,5] The possibility of using
pyridoxal as an alkylating agent was demonstrated in reactions
with phenols and polyphenols.[6] Under the conditions of
the Abramov reaction a-hydroxyphosphonates, existing as
internal salts, in which the positive charge is located at
nitrogen atom, whereas the negative charge – on oxygen atom
were obtained.[1]
Similarly, reactions of furopyridines 1a,b with aliphatic and
aromatic carboxylic acid chlorides occur with the formation of
the compounds 5a–d (Scheme 2).
Funding
This work was supported by the Russian Foundation for Basic
Research (project no. 18-03-00061).
ORCID
Lyudmila K. Kibardina
Roza Kh. Bagautdinova
Alexey V. Trifonov
http://orcid.org/0000-0002-6035-2118
http://orcid.org/0000-0002-0101-9411
http://orcid.org/0000-0002-2178-118X
By the functionalization of 1-alkoxy or 1-dialkylaminofur-
opidines on the basis of pyridoxal the new biologically active
Scheme 1 Reactions of amino(alkoxy)furopyridines with diphenylchlorophosphine sulfide and 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-sulfide.
CONTACT Lyudmila K. Kibardina
kibardina@iopc.ru
Arbuzov Institute of Organic and Physical Chemistry
, FRC Kazan Scientific Center of RAS, Arbuzov
Str. 8, Kazan, 420088, Russia.
ß 2018 Taylor & Francis Group, LLC

2
L. K. KIBARDINA ET AL.
Alkoxy-7-Hydroxy-1,3-Dihydrofuro[3,4-c]Pyridinium
Salts.
Russ. J. Org. Chem. 2018, 54, 578–581. DOI: 10.1134/
S1070428018040103.
[3] Kibardina, L. K.; Trifonov, A. V.; Burilov, A. R.; Pudovik,
M. A.; Dobrynin, A. B.; Pudovik, E. M. Phosphorus-Containing
Salts Derived from Pyridoxal. Russ. J. Org. Chem. 2015, 51,
1510–1512. DOI: 10.1134/S1070428015100280.
[4] Kibardina, L. K.; Bagautdinova, R. H.; Dobrynin, A. B.; Burilov,
A. R.; Pudovik, M. A.; Trifonov, A. V.; Pudovik, E. M.
Pyridoxal Reactions with Amines and Aliphatic Diamines. Russ.
J. Gen. Chem. 2016, 86, 607–612. DOI: 10.1134/
S1070363216030178.
Scheme 2 Reactions of diethylamino(ethoxy)furopyridines with chlorides of ali-
phatic and aromatic carboxylic acids.
[5] Kibardina, L. K.; Burilov, A. R.; Pudovik, M. A.; Trifonov,
A. V.; Pudovik, E. M. Pyridoxal-Derived Schiff’s Bases. Russ. J.
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