Next Article in Journal
2-(4-(Dimethylamino)phenyl)-3,3-difluoro-4,6-diphenyl-3,4-dihydro-1,2,4,5,3-tetrazaborinin-2-ium-3-ide
Previous Article in Journal
7,7’-(4,4-Bis(2-ethylhexyl)-4H-cyclopenta[2,1-b:3,4-b’]dithiophene-2,6-diyl)bis(4-bromobenzo[c][1,2,5]thiadiazole)
Communication

Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

1
Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006 Riga, Latvia
2
Institute of Organic Chemistry, National Academy of Science of Ukraine, Murmanska Str. 5, 02660 Kiev, Ukraine
*
Author to whom correspondence should be addressed.
Academic Editor: Panayiotis A. Koutentis
Molbank 2022, 2022(1), M1311; https://doi.org/10.3390/M1311
Received: 8 December 2021 / Revised: 20 December 2021 / Accepted: 22 December 2021 / Published: 24 December 2021
(This article belongs to the Section Organic Synthesis)
In the present work, construction of double-charged cationic amphiphilic 1,1′-{[3,5-bis(dodecyl¬oxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide (7) was performed in four steps. Dodecyl 3-oxobutanoate (1) was condensed with thiophene-3-carbaldehyde (2) which was necessary for Hantzsch cyclisation dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3). Two-component Hantzsch type cyclisation of dodecyl (E/Z)-3-aminobut-2-enoate (4) and dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3) gave 3,5-bis(dodecyloxycarbonyl)-2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine (5). Bromination of compound 5 followed by nucleophilic substitution of bromine with pyridine gave the desired cationic amphiphilic 1,4-dihydropyridine 7. The obtained target compound 7 and new intermediates 3, 5 and 6 were fully characterised by IR, UV, 1H NMR, 13C NMR, HRMS or microanalysis. Characterisation of nanoparticles formed by the cationic 1,4-dihydropyridine 7 in an aqueous solution was performed by DLS measurements. View Full-Text
Keywords: 1,4-dihydropyridines; DLS; nanoparticles; self-assembling properties; synthetic lipids 1,4-dihydropyridines; DLS; nanoparticles; self-assembling properties; synthetic lipids
Show Figures

Scheme 1

MDPI and ACS Style

Rucins, M.; Pajuste, K.; Plotniece, A.; Pikun, N.; Rodik, R.; Vyshnevskiy, S.; Sobolev, A. Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide. Molbank 2022, 2022, M1311. https://doi.org/10.3390/M1311

AMA Style

Rucins M, Pajuste K, Plotniece A, Pikun N, Rodik R, Vyshnevskiy S, Sobolev A. Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide. Molbank. 2022; 2022(1):M1311. https://doi.org/10.3390/M1311

Chicago/Turabian Style

Rucins, Martins, Karlis Pajuste, Aiva Plotniece, Nadiia Pikun, Roman Rodik, Sergiy Vyshnevskiy, and Arkadij Sobolev. 2022. "Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide" Molbank 2022, no. 1: M1311. https://doi.org/10.3390/M1311

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop