Data for the synthesis and characterisation of 2,6-di(bromomethyl)-3,5-bis(alkoxycarbonyl)-4-aryl-1,4-dihydropyridines as important intermediates for synthesis of amphiphilic 1,4-dihydropyridines

This data file describes the synthetic protocol for preparation of the original 2,6-di(bromomethyl)-3,5-bis(alkoxycarbonyl)-4-aryl-1,4-dihydropyridines. In total, 6 unpublished compounds were obtained and characterised. The 2,6-di(bromomethyl)-1,4-dihydropyridines are mainly used as intermediates for synthesis of various lipid-like compounds based on 1,4-dihydropyridine cycle. All the structures of 2,6-di(bromomethyl)-1,4-dihydropyridines were confirmed by Nuclear Magnetic Resonance (NMR, including 1H NMR and 13C NMR) data. The data provided herein are directly related to the previously published research article – “Novel cationic amphiphilic 1,4-dihydropyridine derivatives for DNA delivery” [1] where three derivatives (2,6-di(bromomethyl)-4-phenyl-1,4-dihydropyridines 2a-c) from six presented in this data file were used as starting materials in synthesis of amphiphilic 1,4-dihydropyridines without any purification and characterisation. Synthesis of other three 2,6-di(bromomethyl)-3,5-bis(alkoxycarbonyl)-4-aryl-1,4-dihydropyridines 2d-f and their characterisation are reported herein at the first time. Information provided in this data file can be used in organic synthesis by other chemists to develop synthetic strategies for the construction of various cationic 1,4-dihydropyridine derivatives and related heterocycles.


a b s t r a c t
This data file describes the synthetic protocol for preparation of the original 2,6-di(bromomethyl)-3,5-bis(alkoxycarbonyl)-4-aryl-1,4-dihydropyridines. In total, 6 unpublished compounds were obtained and characterised. The 2,6-di(bromomethyl)-1,4-dihydropyridines are mainly used as intermediates for synthesis of various lipid-like compounds based on 1,4-dihydropyridine cycle. All the structures of 2,6di(bromomethyl)-1,4-dihydropyridines were confirmed by Nuclear Magnetic Resonance (NMR, including 1 H NMR and 13 C NMR) data. The data provided herein are directly related to the previously published research article -"Novel cationic amphiphilic 1,4-dihydropyridine derivatives for DNA delivery" [1] where three derivatives (2,6-di(bromomethyl)-4-phenyl-1,4-dihydropyridines 2a-c ) from six presented in this data file were used as starting materials in synthesis of amphiphilic 1,4-dihydropyridines without any purification and characterisation. Synthesis of other three 2,6-di(bromomethyl)-3,5-bis(alkoxycarbonyl)-4-aryl-1,4-dihydropyridines 2d-f and their characterisation are reported herein at the first time. Information provided in this data file can be used in organic synthesis by other chemists to develop synthetic strategies for the construction of various cationic 1,4-dihydropyridine derivatives and related heterocycles.
© 2020 The Author(s

Value of the data
• The data contains the general synthetic procedure for bromination of the methyl groups of 3,5-bis(alkoxycarbonyl) −2,6-dimethyl-4-aryl-1,4-dihydropyridine which may serve as valuable guidance for organic chemists. • The obtained 2,6-di(bromomethyl) −1,4-dihydropyridines can be used as intermediates for synthesis of various lipid-like compounds based on 1,4-dihydropyridine cycle. • The data provides characterisation of original compounds -2,6-di(bromomethyl) −3,5bis(alkoxycarbonyl) −4-aryl-1,4-dihydropyridines which have not been reported before. • Additionally, described synthetic procedure and obtained spectral data will be useful for preparation and structure elucidation of brominated derivatives in related heterocyclic systems. • Besides the use of 2,6-di(bromomethyl) derivatives in synthesis of cationic 1,4dihydropyridines their applications may be extended to other reactions of bromomethyl groups.  ( Table 1 ).
In the case of comp. 2a,b the yellow precipitate was filtered off and washed with water; for the comp. 2c-f the solvent was evaporated and the residue was purified by flashchromatography. The compounds 2d-f compounds were found to be unstable during the storage due to lactonisation into 8-aryl-5,8-dihydro-1 H ,3 H -difuro[3,4-b :3 ,4 -e ]pyridine-1,7(4 H )dione derivatives [4] . Satisfactory NMR data were obtained after two purifications by chromatography.

Declaration of Competing Interest
The author declare that they have no known competing financial interests or personal relationships that could appeared to influence the work reported in this paper.