Synthesis of phosphonium and ammonium derivatives of benzo-crown ethers and their cholinolytic activity

Lukoyanov, Nikolay; Vanikin, G. I.; Malygin, V. V.; Kal'chenko, V. I.; Parkhomenko, N. A.; Atamas, L. I.; Pacheva, L. M.; Galenko, T. G.; Иванова, Т. А.; Panarin, V. A.; Raevskii, O. A.; Markovskii, L. N.

doi:10.1007/bf00766361

Cited by 5 publications

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“…Precooling BCE hydrochloric acid solution to 0 °C, and the careful addition to it the chilled sodium hypochlorite solution at a rate at which the temperature of the reaction mixture did not exceed 5 °C yielded good crystallized products. But contrary to the expected, dichlorides were absent and pure products of aromatic ring exhaustive chlorination were formed -3'4',5'6'-tetrachloroBCE (7)(8)(9). Therefore the optimized reaction conditions (excess NaClO in solution of HCl (pH <1, 0-5 °C, 24 h) allowed hypochlorite to use the most of it's chlorinating potential.…”

Section: Resultsmentioning

confidence: 81%

“…Sufficient mobility of bromine and iodine atoms in the aromatic fragments of these macrocycles enables ease of further transformations into acetylene, [3][4][5] vinyl, [4][5] n-alkyl, n-hydroxyalkyl, [6] bioactive ammonium and phosphonium [7] derivatives, which are hard or inaccessible by other ways, and also crown heterocycles, [8] bis-benzocrown ethers, [3,6] etc. HBCE have great potential as materials for the synthesis of new types of polymers with selective sorption, [9] original nanolayers, [1] considerably increasing products' wear resistance, etc.…”

Section: Introductionmentioning

confidence: 99%

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Halogenation of Benzocrown Ethers by Hypohalites in Aqueous Solutions

Pluzhnik-Gladyr¹

2012

MHC

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Section: Resultsmentioning

confidence: 81%

Section: Introductionmentioning

confidence: 99%

Halogenation of Benzocrown Ethers by Hypohalites in Aqueous Solutions

Pluzhnik-Gladyr¹

2012

MHC

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“…Under the same conditions as MePPh 2 , the quaternization of BnPPh 2 provided phosphonium salts 4a–e in 48–83% yields. Several isolated examples have been reported for the quaternization of BnPPh 2 with aryl halides by using the early Ni-catalyzed methods. − …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Aryldiphenylphosphine Oxides by Quaternization of Tertiary Diphenylphosphines with Aryl Bromides Followed by the Wittig Reaction

Zhong

Huang

2020

ACS Omega

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A two-step method for the synthesis of aryldiphenylphosphine oxides from tertiary diphenylphosphines and aryl bromides is developed. The first step is the quaternization of methyldiphenylphosphine or benzyldiphenylphosphine with aryl bromides. This quaternization can be nickel-catalyzed (metal-free in some cases), and tolerate of a variety of functional groups, furnishing quaternary phosphonium salts in 48−90% yields. The second step is Wittig reactions of these quaternary phosphonium salts with furan-2-carbaldehyde or p-chlorobenzaldehyde to provide aryldiphenylphosphine oxides in 27−90% yields. The use of the Wittig reaction for the synthesis of tertiary phosphine oxides is in contrast to its traditional use for the synthesis of olefins, leaving tertiary phosphine oxide as a byproduct. This quaternization−Wittig method can be applied to synthesize aryldiphenylphosphine oxides that are difficult to access by the alkaline hydrolysis of aryltriphenylphosphonium salts, especially those bearing an electron-deficient aryl group. The ligand-coupling mechanism for the alkaline hydrolysis of (p-acylphenyl)triphenylphosphonim salts is also discussed.

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“…Иодзамещенные бензо-(БКЭ) и дибензокраунэфиры (ДБКЭ) легко трансформируются в труднодоступные ацетиленовые, [1][2][3] винильные, [4,5] н-алкильные, н-гидроксиалкильные, [6] биологически активные аммониевые и фосфониевые [7] производные, а также краун-гетероциклы, [8] бис-бензокраун-эфиры [3,6] и др.…”

Section: Introductionunclassified

A Simple Method for Iodination of Benzo- and Dibenzocrown Ethers

Pluzhnik-Gladyr¹,

Ракипов²,

Kotlyar³

2009

MHC

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Иодирование бензо-12-краун-4, бензо-15-краун-5 и бензо-18-краун-6 эквимолярными количествами N-иодсукцинимида протекает быстро и селективно в среде этанола в присутствии небольших количеств серной кислоты и приводит к соответствующим 4 I-иодпроизводным с выходами 78-86%. Реакционная способность [3.3]дибензо-18-краун-6 мало отличается от таковой у бензокраун-эфиров, а дииодид (смесь цис-и транс-изомеров) образуется с выходом 76%.

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Synthesis of phosphonium and ammonium derivatives of benzo-crown ethers and their cholinolytic activity

Cited by 5 publications

References 0 publications

Halogenation of Benzocrown Ethers by Hypohalites in Aqueous Solutions

Halogenation of Benzocrown Ethers by Hypohalites in Aqueous Solutions

Synthesis of Aryldiphenylphosphine Oxides by Quaternization of Tertiary Diphenylphosphines with Aryl Bromides Followed by the Wittig Reaction

A Simple Method for Iodination of Benzo- and Dibenzocrown Ethers

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