A New One-Pot Synthesis of Double-Armed Ionizable Crown Ethers Using the Mannich Reaction

Chi, Ki‐Whan; Wei, Han-Chao; Kottke, Thomas; Lagow, Richard J.

doi:10.1021/jo960332f

Cited by 40 publications

(23 citation statements)

References 15 publications

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“…Materials L 1 -L 3 were prepared in one step using a known procedure 19 based on alkylation of the 1,10-diaza-18-crown-6 parent membered macrocycles with para-substituted hydroxybenzyl halide. Poly(vinyl chloride) (PVC; secondary standard), potassium tetrakis (p-chlorophenyl)borate (KTpClPB), and tris(hydroxymethyl)aminomethane (Tris) were purchased from Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Double-armed crown ethers: Synergic π-coordination effect on potentiometric sensing for Ag(i)

Choi

Yoon

Kim

et al. 2002

Analyst

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Three diaza-18-crown-6 derivatives having methyl (L1), methoxy (L2) and phenyl (L3) end-groups in para-substituted phenolic side-arms have been investigated as potentiometric sensing materials for silver(I)-selective poly(vinyl chloride) membrane electrodes. The aim of the present work is to establish whether a combination of macrocyclic coordination to Ag+ ion and Ag-pi interaction might produce synergic effect in Ag+ ion sensing. The electrode based on the aromatic end-groups, L3 was found to give remarkably better electrochemical performance than their aliphatic counterparts (L1 and L2). The sensing ability for Ag+ ion with the proposed electrode was enhanced noticeably due to the pi-coordination of Ag+ ion, which was elucidated by NMR. The present findings may serve as an alternative approach for designing advanced sensing materials.

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Section: Methodsmentioning

confidence: 99%

Double-armed crown ethers: Synergic π-coordination effect on potentiometric sensing for Ag(i)

Choi

Yoon

Kim

et al. 2002

Analyst

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“…The bis(8-hydroxyquinolin-7-ylmethyl)-substituted diazacrown ethers 25-32 were prepared by treating the diazacrowns with the appropriate 8-hydroxyquinoline and paraformaldehyde (Scheme 2) [20,[25][26][27]. Ligand 33 containing two 8-hydroxyquinolin-2-ylmethyl substituents was prepared by the reductive amination process [19,27,28] as shown in Scheme 3.…”

Section: Introductionmentioning

confidence: 99%

New diazadi(and tri)thia‐21‐crown‐7 ethers containing 8‐hydroxyquinoline side arms

Song

Chen

Ji-guo

et al. 2001

Journal of Heterocyclic Chem

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A series of macrocyclic diazadi(and tri)thiacrown ethers containing two 5-substituent-8-hydroxyquinoline side arms have been synthesized from the corresponding macrocyclic diazadi(and tri)thiacrown ethers. The crown ethers were obtained by reduction of the proper macrocyclic di(and tri)thiadiamides by boranetetrahydrofuran or by sodium borohydride-boron trifluoride ethyl etherate-tetrahydrofuran. The yields for the reduction of diamides by sodium borohydride-boron trifluoride ethyl etherate-tetrahydrofuran were higher than those by borane-tetrahydrofuran. The following four methods were used to prepare macrocycles bearing two 8-hydroxyquinoline side arms: (1) Mannich reaction with 8-hydroxyquinoline; (2) Reductive amination with 8-hydroxyquinoline-2-carboxaldehyde using sodium triacetoxyborohydride as the reducing agent; (3) Cyclization of N,N'-bis(8-hydroxyquinolin-2-ylmethyl)-1,2-bis(2-aminoethoxy)ethane (38) with bis(α-chloroamide) 5; and (4) A step-by-step process wherein macrocyclic trithiadiamide 11 was reduced by lithium aluminum hydride-tetrahydrofuran to the cyclic monoamide 36, which smoothly reacted with 5-chloro-8-hydroxyquinoline to produce monosubstituted-macrocyclic monoamide 39.

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“…Mannich aminomethylation has been used to attach HQ and CHQ groups to the azacrown ethers through HQ and CHQ 7-positions. 3,7,[13][14][15] In the present case, the appropriate diazadithiacrown ether 16-22 and the appropriate HQ derivative were treated with paraformaldehyde in refluxing benzene in the one-step aminomethylation reaction 3,7,16,17 to give the bis(2-or 5-substituted-8-quinolin-7-ylmethyl)-substituted ligands 23-32 (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Syntheses of diazadithiacrown ethers containing two 8-hydroxyquinoline side arms

Song¹,

Bradshaw²,

Chen³

et al. 2001

Arkivoc

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This paper is dedicated to Professor Miha AbstractTen new diazadithiacrown ethers containing two 8-hydroxyquinoline (HQ) sidearms attached through the HQ 7-positions and four new diazadithiacrown ethers containing two HQ sidearms attached through the HQ 2-positions have been prepared. Some of these new ligands also contain a hydroxymethyl substituent. The starting macrocyclic diazadithiacrown ethers were obtained by treatment of a bis(α-chloroamide) with the appropriate dimercaptan using K 2 CO 3 as the base followed by reduction of the resulting macrocyclic dithiadiamide by BH 3 -THF or by NaBH 4 in the presence of BF 3 -ether as a catalyst. HQ-containing ligands 23-32 were synthesized by a Mannich reaction of the secondary macrocyclic diamines with the substituted-8-hydroxyquinoline. HQ-containing ligands 33-36 were prepared by reductive amination of the secondary macrocyclic diamines with 8-hydroxyquinoline-2-carbaldehyde. The HQ-containing diazadithiacrown ethers which also contain a hydroxymethyl group on the macroring 23-29, 33, and 35 are more soluble in polar solvents than those without the hydroxymethyl group.

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A New One-Pot Synthesis of Double-Armed Ionizable Crown Ethers Using the Mannich Reaction

Cited by 40 publications

References 15 publications

Double-armed crown ethers: Synergic π-coordination effect on potentiometric sensing for Ag(i)

Double-armed crown ethers: Synergic π-coordination effect on potentiometric sensing for Ag(i)

New diazadi(and tri)thia‐21‐crown‐7 ethers containing 8‐hydroxyquinoline side arms

Syntheses of diazadithiacrown ethers containing two 8-hydroxyquinoline side arms

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