2001
DOI: 10.1016/s0143-7208(01)00026-2
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Synthesis and spectroscopic properties of new Schiff bases containing the N-phenylaza-15-crown-5 moiety

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Cited by 15 publications
(8 citation statements)
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“…In the same work 5 on the synthesis of 4-(aza-15-crown-5) benzocarbaldehyde (3), the use of a modified four step synthetic procedure was described. 6 Led by the will to create an economical, reproducible and simple synthetic scheme through the combination of a few known methods, [5][6][7][8] in this work a new, more robust, easy-to-implement, cost-effective and only two-step procedure was created for the preparation of intermediate 3 (Scheme 1B). The crucial optimisation step in this procedure is the neutralization of the reaction mixture after the Vilsmeier-Haack-Arnold reaction, with the milder reagent, sodium acetate instead of the aggressive sodium hydroxide 8 which is reported to cause ring opening and damage of the crown functionality (TLC monitoring, NMR).…”
Section: Synthesismentioning
confidence: 99%
See 1 more Smart Citation
“…In the same work 5 on the synthesis of 4-(aza-15-crown-5) benzocarbaldehyde (3), the use of a modified four step synthetic procedure was described. 6 Led by the will to create an economical, reproducible and simple synthetic scheme through the combination of a few known methods, [5][6][7][8] in this work a new, more robust, easy-to-implement, cost-effective and only two-step procedure was created for the preparation of intermediate 3 (Scheme 1B). The crucial optimisation step in this procedure is the neutralization of the reaction mixture after the Vilsmeier-Haack-Arnold reaction, with the milder reagent, sodium acetate instead of the aggressive sodium hydroxide 8 which is reported to cause ring opening and damage of the crown functionality (TLC monitoring, NMR).…”
Section: Synthesismentioning
confidence: 99%
“…The T m = 44-45 1C (literature: 44-45 1C). 7 Synthesis of 4-aza-15-crown-5-benzaldehyde (3) N-Phenylaza-15-crown-5 (2g) (2 g, 0.0068 mol) was dissolved in 6 ml of dimethylformamide (DMF). After cooling to À10 1C, the amount of 1.04 g (0.62 ml, 0.0068 mol) phosphohenoxy chloride were added dropwise and the reaction mixture was stirred for 1 h at room temperature and for 4 at 70 1C.…”
Section: Synthesis Of Quaternary Benzothiazolium Salts 2a-2dmentioning
confidence: 99%
“…Synthesis of the azacrown derivatives PA15C5 and 4APA15C5 was carried out according to literature [15][16][17]. To confirm their proposed structure, detailed characterization techniques such as FT-IR, 1 H NMR, 13 C NMR, and DEPT were used.…”
Section: Resultsmentioning
confidence: 99%
“…This compound was prepared by the modification of the procedure reported in the literature [15]. N-phenylaza-15-crown-5 sodium perchlorate monohydrate (14 g) was decomposed by treatment with a mixture of CH 2 Cl 2 :H 2 O (1:1), the organic layer was separated, dried, and evaporated to give N-phenylaza-15-crown-5, 7 g of (73%), mp.…”
Section: N-phenylaza-15-crown-5 [Pa15c5]mentioning
confidence: 99%
“…This compound was prepared according to the literature procedure [29, 30] N-(4-nitrosophenyl)aza-15-crown-5 (1.60 g, 4.90 mmol) was dissolved in 3 mL hydrochloric acid (37%) and 1.6 mL water. SnCl 2 (2.60 g, 14.00 mmol) was then added in portions under stirring at 40°C.…”
Section: Methodsmentioning
confidence: 99%