Tricyclic flavonoids with 1,3-dithiolium substructure

Abstract

SummaryThe synthesis of new 3-dithiocarbamic flavonoids has been accomplished by the reaction of the corresponding 2-hydroxyaryl dithiocarbamates with aminals. These flavonoids were obtained as a mixture of diastereoisomers, the anti isomer being the major one. The heterocyclization of these compounds provided novel tricyclic flavonoids bearing a 1,3-dithiolium-2-yl ring fused at the 3,4-carbon positions of the benzopyran moiety.

Proton-Initiated Conversion of Dithiocarbamates of 9,10-Anthracenedione

“…This agrees with the data on the greater propensity to protonate the thiocarbonyl group in strong acids compared to the nitrogen atom in the dithiocarbamate fragment [13]. The characteristic signals of the dithiocarbonyl substituent and the anthracenedione fragment are retained in the 1 H and 13 C NMR spectra of the obtained compounds, suggesting that there are no transformations of dithiocarbamates 1-5 in the mesoionic structure, as described in [9].…”

“…It is known the structural modification of the dithiocarbamate fragment opens up wide possibilities for the obtaining of a number of heterocyclic derivatives [4]. The interaction of organic dithiocarbamates with a mixture of H 2 SO 4 -AcOH under acid-catalyzed cyclodehydration leads to the formation of mesoionic salts of dithiolium [9]. In recent years, this direction was developed by a group of Romanian researchers [10].…”

Novel Synthetic Strategy of Cyclic Dithiocarbamates Catalyzed by Triton-B

“…Furthermore, it has been comprehended through a number of available reports that biological activities of molecules increase diversely by incorporating dithiocarbamate moiety into it [22]. Organic dithiocarbamates have been used as the synthon for various synthesis [23][24][25][26][27][28][29][30][31][32] etc. and considered as the important biological moiety.…”

New 4-(4-Hydroxyaryl)-5-Methyl-1,3-Dithiol-2-ylidene Derivatives

“…Moreover, novel dye-sensitized solar cells based on 1,3-dithiol-2-ylidene derivatives have been recently reported [9]. For these reasons heterocyclic compounds -especially those containing sulfur -represent an important resource for the material chemistry and not only [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25]. An important precursor for 1,3-dithiol-2ylidene derivatives are the 1,3-dithiolium-2-yl compounds.…”