New Chromogenic Azothiacrown Ethers — Synthesis and Properties.

Abstract

New Chromogenic Azothiacrown Ethers -Synthesis and Properties. -The new macrocycles, e.g. (V) and (VI), are prepared by the route shown in the scheme and applied as ion carriers in ion-selective membrane electrodes.Some stability constants are determined. -(SZCZYGELSKA-TAO, J.; BIERNAT, J. F.; Pol. J. Chem. 76 (2002) 7, 931-936; Dep. Chem. Technol., Tech. Univ. Gdansk, PL-80-952 Gdansk, Pol.; EN)

BINOL Macrocycle Derivatives: Synthesis of New Dinaphthyl Sulfide Aza Oxa Thia Crowns (Lariats)

“…Chloroamide derivatives (4-7) were synthesized from the reaction of corresponding amine and chloroacetyl chloride in the presence of triethylamine as base and in dichloromethane as solvent (Scheme 2) [40][41][42]45], the lariat azacrowns (8)(9)(10)(11) were synthesized from the reaction of chloroamides (4-7) and macrocycle (3). is reaction was carried out via a modi�ed procedure in the presence of sodium carbonate and catalytic amounts of sodium iodide in CH CN/DMF (10 : 1) at room temperature (Scheme 3) [46][47][48].…”

“…To summarize, we prepared a dinaphthyl sul�de aza crown, and then new dinaphthyl sul�de aza lariats (8)(9)(10)(11) were prepared from the reaction of aza crown and some prepared chloroamides. is lariat is important receptors with naphthalene, quinolone, and azo groups.…”

“…. is chloroamide (4) was prepared from the reaction of aniline and chloroacetyl chloride based on the general procedure (1) (8)(9)(10)(11). To macrocycle (3) (1 mmol, 0.50 g) in acetonitrile (50 mL) alkylating agents were added (one of the chloroamides (4-7) for each reaction) (1 mmol), sodium carbonate (1 mmol, 0.14 g), sodium iodide (catalytic), and dimethylformamide (DMF, 5 mL).…”

“…Since the initial publications on the synthesis of crown ethers and their metal salt complexation properties [1,2], the in�uence of structural variation within such ligands has received increasing attention [3][4][5][6][7][8][9][10][11][12]. One such structural variation is the replacement of one ether oxygen with nitrogen to give an azacrown ether [13,14] or sulfur group to obtain thiacrown ether [14,15].…”

“…Synthesis of 7,10,13-Triaza-1-thia-16,4-dioxa-10-(3aza-2-oxo-3-phenyl propyl)-6,14-dioxo-2,3;17,18-dinaphthocyclooctadecane (11). is aza crown (11) was synthesized from the reaction of macrocycle (3) and aniline chloroamide (4) based on the general procedure (2) and puri�ed by column chromatography on silica gel using CHCl 3 /Methanol (4 : 1) as eluent, the yield was 89% and mp 222-223 ∘ C; IR (KBr): 3385, 3054, 2936, 1688, 1679, 1623, 1601, 1558, 1540, 1503, 1446, 1323, 1263, 1225, 1152, 1079, 765 cm −1 ; 1 H NMR (300 MHz, DMSO-d 6 ) : 3.49 (b, 4H), 3.62 (s, 4H), 4.27 (b, Synthesis of lariats(8)(9)(10)(11). Proposed mechanism for the formation of macrocycle (3).…”