Synthesis of carbomethoxymethylidene cyclopentenedione derivatives based on oxidative cleavage reactions of the allylic double bond 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)-cyclopent-4-en-1,3-dione

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

The reactions of oxidative cleavage of the allyl double bond of 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)-cyclopent-4-ene-1,3-dione in the systems OsO4–NaIO4 and KMnO4–Et3BnN+Cl- were studied. It was shown that the intermediate aldehyde formed at the stage of periodate cleavage of the indicated 2-allylcyclopentene-1,3-dione was oxidized by the Jones reagent and, with subsequent elimination of HCl, was converted into the target 2-carbomethoxymethylidenecyclopent-4-ene-1,3-dione. In an alternative approach, permanganate oxidation of the basic 2-allylcyclopentene-1,3-dione leads to the corresponding diol in moderate yield.

Full Text

Restricted Access

About the authors

V. A. Egorov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: fangim@anrb.ru
ORCID iD: 0000-0001-9710-265X
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

L. S. Khasanova

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: fangim@anrb.ru
ORCID iD: 0000-0002-7183-4200
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

F. A. Gimalova

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Author for correspondence.
Email: fangim@anrb.ru
ORCID iD: 0000-0002-5176-1227
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

M. S. Miftakhov

Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences

Email: fangim@anrb.ru
ORCID iD: 0000-0002-0269-7484
Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

References

  1. Ахметвалеев Р.Р., Акбутина Ф.А., Иванова Н.А., Мифтахов М.С. Изв. АН. Сер. хим. 2001, 1417–1435. [Akhmetvaleev R.R., Akbutina F.A., Ivanova N.A., Miftakhov M.S. Russ. Chem. Bull., Int. Ed. 2001, 50, 1489–1509.] doi: 10.1023/A:1013038427455
  2. Egorov V.A., Gimalova F.A., Zileeva Z.R., Zainullina L.F., Vakhitova Yu.V., Miftakhov M.S. Mendeleev Commun. 2019, 29, 174–175. doi: 10.1016/j.mencom.2019.03.019
  3. Hori H., Nagasawa H., Ishibashi M., Uto Y., Hirata A., Saijo K., Ohkura K., Kirk K.L., Uehara Y. Bioorg. Med. Chem. 2002, 10, 3257–3265. doi: 10.1016/S0968-0896(02)00160-8
  4. Гилязетдинов Ш.Я., Юсупова З.Ф., Саитова М.Ю., Зарудий Ф.С., Ахметвалеев Р.Р., Мифтахов М.С., Акбутина Ф.А., Торосян С.А. Пат. 2144767 (1997). РФ. Б.И. 2000, №3.
  5. Хейнс А. Методы окисления органических соединений. М: Мир, 1988. [Haines A.H. Methods for the Oxidation of Organic Compounds: Alkanes, Alkenes, Alkynes. London: Acad. Press Inc, 1985].
  6. Акбутина Ф.А., Торосян С.А., Востриков Н.С., Спирихин Л.В., Мифтахов М.С. Изв. АН. Сер. хим. 1996, 2961–2963. [Akbutina F.A., Torosyan S.A., Vostrikov N.S., Miftakhov M.S. Russ. Chem. Bull. 1996, 45, 2813–2815.] doi: 10.1007/BF01430649
  7. Fatiadi A.J. Synthesis. 1987, 85–127. doi: 10.1055/s-1987-27859

Supplementary files

Supplementary Files
Action
1. JATS XML
Download
2. Fig. Biologically active cyclopentene-1,3-diones 8, 9 [3] and carbomethoxymethylidencyclopentenone 10 [4].

Download (70KB)
Indexing metadata
3. Scheme

Download (184KB)
Indexing metadata
4. Synthesis of carbomethoxymethylidencyclopentenedione derivatives based on oxidative cleavage reactions of the allylic double bond 2-allyl-2,4-dichloro-5-(2,4,6-trimethoxyphenyl)cyclopent-4-ene-1,3-dione

Download (106KB)
Indexing metadata

Copyright (c) 2024 Russian Academy of Sciences