The monograph deals with unexpected rearrangements of β-aminopropioamidoxime derivatives, which form previously unknown spiropyrazolinium compounds.
Recently we found that the 3,5-substituted 1,2,4-oxadiazoles, which are derivatives of β-aminopropioamidoximes, are of interest for practical medicine since they possess local anaesthetic, anti-tubercular and anti-diabetic properties.
But when analyzing biological activity, it is necessary to take into account the chemical stability of the studied compounds. It turned out that 3,5-substituted 1,2,4-oxadiazoles taken for screening according to the Boughton–Katritzky rearrangement scheme are easily transformed into previously unknown spiropyrazolinium compounds and, thus, the pronounced biological activity observed in practice, should be attributed to them.
In addition, when studying the reactivity of β-aminopropioamidoximes in the arylsulfochlorination reaction, it was found that salts (chlorides and arylsulfonates) of spiropyrazolinium compounds are instantly formed without isolating of the expected O-sulfoaryl-β-aminopropioamidoximes. The monograph describes this interesting structural feature of β-aminopropioamidoximes - to form spiropyrazolinium systems with a rich potential for biologically useful properties.
About the authors
Lyudmila Alexandrovna Kayukova is a Chief Researcher of the JSC «A.B. Bekturov Institute of Chemical Sciences», Doctor of Chemical Sciences, Professor (Almaty, Kazakhstan). She graduated from Leningrad State University, Department of Physical Organic Chemistry (Leningrad, Russia). Her current and previous research interests are medical organic chemistry, structure of organic compounds. She is the member of the editorial board of the Institutional Chemical Journal of Kazakhstan and the member of the Academic Council of the Institute. She is a scientific head of 8 candidate and PhD dissertations.
Anna Vladimirovna Vologzhanina is a senior researcher of INEOS RAS (Moscow, Russia). She received M.D. of the Samara University in 2003 and Ph.D. in 2006. She worked as a crystallographer of INEOS RAS since 2007 till now. Her research interests include crystallography of small molecules and coordination compounds, topological analysis, charge density studies and solid state reactions. She received L’Oreal-Unesco award for Women in Science (Russia, 2014).
Elmira Murzabayevna Yergaliyeva is a junior researcher of the JSC «A.B. Bekturov Institute of Chemical Sciences» (Amaty, Kazakhstan) (2020‒2022). She is a PhD student of the Al-Farabi Kazakh National University, specializing in Chemical Technology of Organic Substances (2019‒2022) (Amaty, Kazakhstan). Her research interests include chemistry of heterocyclic compounds and quantum chemical research methods in organic chemistry. Publications: articles in the journals of Web of Science and Scopus databases, Chemical Journal of Kazakhstan, abstracts of reports on the international and republic conferences and utility model patents of the Republic of Kazakhstan on the anti-diabetic properties of β-aminopropioamidoximes.
Bibliographic Information
- DOI: https://doi.org/10.51580/2022-ebook.01
- Publisher: Daryn, Almaty, Kazakhstan
- Copyright Information: JSC «A.B. Bekturov Institute of Chemical Sciences»
- ISBN: 978-601-08-1472-1
- Number of Pages: 156
- Number of Illustrations: 35 black/white illustrations, 21 illustrations in colour
- Title of chapters:
Chapter 1
RAPID ACID HYDROLYSIS OF 5-ARYL-3-(β-THIOMORPHOLINOETHYL)-1,2,4-OXADIAZOLES
Chapter 2
RAPID BOULTON–KATRITZKY REARRANGEMENT OF 5-ARYL-3-[2-(PIPERIDIN-1-YL)ETHYL]-1,2,4-OXADIAZOLES UPON EXPOSURE TO WATER AND HCL
Chapter 3
BOULTON-KATRITZKY REARRANGEMENT OF 5-SUBSTITUTED PHENYL-3-[2-(MORPHOLIN-1-YL)ETHYL]-1,2,4-OXADIAZOLES AS A SYNTHETIC PATH TO SPIROPYRAZOLINE BENZOATES AND CHLORIDE WITH ANTITUBERCULAR PROPERTIES
Chapter 4
ARYLSULFOCHLORINATION OF β-AMINOPROPIOAMIDOXIMES GIVING
2-AMINOSPIROPYRAZOLYLAMMONIUM ARYLSULFONATES
Chapter 5
ARYLSULPHONATES OF SPIROPYRAZOLINES AND O-TOSYLATE-β-(BENZIMIDAZOL-1-YL)PROPIOAMIDOXIME AS THE PRODUCTS OF β-AMINOPROPIOAMIDOXIMES TOSYLATION
Chapter 6
REDETERMINATION OF THE STRUCTURE OF 2-AMINO-8-THIA-1,5-DIAZASPIRO[4.5]DEC-1-EN-5-IUM CHLORIDE MONOHYDRATE
Chapter 7
COMPUTATIONAL STUDIES OF THE PRODUCTS OF TOSYLATION AND
PARA-NITROBENZENESULFOCHLORINATION OF β-AMINOPROPIOAMIDOXIMES
Chapter 8
REACTION PRODUCTS OF β-AMINOPROPIOAMIDOXIMES
NITROBENZENESULFOCHLORINATION: LINEAR AND REARRANGED TO
SPIROPYRAZOLINIUM SALTS WITH ANTIDIABETIC ACTIVITY
Chapter 9
FREE ENERGIES OF 2-AMINO-1,5-DIAZASPIRO[4.5]DEC-1-EN-5-IUM CHLORIDES MONOHYDRATES AND ARYLSULFONATES FORMATION AT β-AMINOPROPIOAMIDOXIMES ARYLSULFOCHLORINATION
