Condensation of secondary amines with CH-acids and formaldehyde under the influence of microwave radiation-Reference-Cited by-同舟云学术

Condensation of secondary amines with CH-acids and formaldehyde under the influence of microwave radiation

Published:2023-03-20 Issue:1 Volume:18 Page:21-28
ISSN:2686-7575
Container-title:Fine Chemical Technologies
language:
Short-container-title:Fine Chem. Technol.

Author:

Musin A. I.¹^ORCID,Sultanova D. S.¹^ORCID,Borisova Yu. G.¹^ORCID,Mudrik T. P.²^ORCID,Daminev R. R.¹^ORCID

Affiliation:

1. Ufa State Petroleum Technological University

2. Center for Grain Quality Assessment

Abstract

Objectives. To synthesize tertiary amines containing gem-dichlorocyclopropane or 1,3-dioxolane fragmentusing the Mannich reaction, as well as obtain ethyl ester of β-aminopropionic acidbydecarboxylation of tert-amine, a derivative of diethylmalonate containing a gem- dichlorocyclopropane fragment.Methods. In order to obtain tertiary amines by the Mannich reaction, the microwave activation method was used. To determine the qualitative and quantitative composition of the reaction masses, gas chromatography, electron ionization mass spectrometry, and 1H-, 13C-nuclear magnetic resonance spectrometry methodswere used.Results. Under microwave radiationconditions, tertiary amines containing gem- dichlorocyclopropane or 1,3-dioxolane fragment were synthesized by condensation of secondary amines, CH-acids, and paraformaldehyde.Conclusions. Tertiary amines containing a gem-dichlorocyclopropane or cycloacetal fragment in their structure were obtainedin high yields under microwave radiation.

Publisher

RTU MIREA

Subject

Inorganic Chemistry,Organic Chemistry,Fluid Flow and Transfer Processes,Process Chemistry and Technology

Reference15 articles.

1. Kuz’mina U.S., Raskil’dina G.Z., Ishmetova D.V., et al. Cytotoxic activity against SH-SY5Y neuroblastoma cells of heterocyclic compounds containing gem-dichlorocyclopropane and/or 1,3-dioxacycloalkane fragments Pharm. Chem. J. 2022;55(12):1293–1298. https://doi.org/10.1007/s11094-02202574-6 [Original Russian Text: Kuz’mina U.S., Raskil’dina G.Z., Ishmetova D.V., et al. Cytotoxic activity against SH-SY5Y neuroblastoma cells of heterocyclic compounds containing gemdichlorocyclopropane and/or 1,3-dioxacycloalkane fragments. Khimiko-Farmatsevticheskii Zhurnal. 2021;55(12):27–32 (in Russ.). https://doi.org/10.30906/0023-1134-2021-55-12-27-32]

2. Stanislawski P.C., Willis A.C., Banwell M.G. gemDihalocyclopropanes as building blocks in natural-product synthesis: enantioselective total syntheses of ent-erythramine and 3-epi-erythramine. Chem. Asian J. 2007;2(9):1127–1136. https://doi.org/10.1002/asia.200700155

3. Genta M.T., Villa C., Mariani E., Loupy A., Petit A., Rizzetto R., Mascarotti A., Morini F., Ferro M. Microwaveassisted preparation of cyclic ketals from a cineole ketone as potential cosmetic ingredients: solvent-free synthesis, odour evaluation, in vitro cytotoxicity and antimicrobial assays. Int. J. Pharm. 2002;231(1):11–20. https://doi.org/10.1016/S03785173(01)00821-3

4. Elshan N.G.R.D., Rettig M.B., Jung M.E. Synthesis of β-amino diaryldienones using the Mannich reaction. Org. Lett. 2019;21(11):4039−4043. https://doi.org/10.1021/acs.orglett.9b01195

5. Jin Y., Su G., Yu J. Mannich reaction as a key strategy for the synthesis of trifluoroethyl derived tertiary and secondary amine. Bull. Korean Chem. Soc. 2021;42(6):836–839. https://doi.org/10.1002/bkcs.12293