One-Pot Synthesis of Fmoc- and Boc-Protected Aza-Methionine Precursors from 2-Methylthioacetaldehyde Dimethyl Acetal

Mastitski, Anton; Järv, Jaak

doi:10.1080/00304948.2014.963460

Cited by 10 publications

(3 citation statements)

References 10 publications

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“…Importantly, the reduction methodology was simplified to avoid expensive catalysts and complicated equipment. Therefore, the developed 'one-pot' synthetic protocol [42,46,54] appears to be a convenient and effective procedure for the preparation of various protected alkylhydrazines from acetals and ketals.…”

Section: Continued On the Next Pagementioning

confidence: 99%

Aza-peptides: expectations and reality

Arujõe¹,

Järv²,

Mastitski³

et al. 2022

PEAS

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The replacement of the α-carbon atom in an α-amino acid structure by a nitrogen atom yields alkylcarbazic acids, also known as α-aza amino acids. Although the topology of α-amino acids and α-aza amino acids is similar, their chemical and stereochemical properties are significantly different. For this reason, the application of the common solid-phase peptide synthesis (SPPS) protocol cannot be used for aza-peptide bond synthesis without changes. On the other hand, the aza-peptide bond is more stable than the common peptide bond, therefore these compounds are very attractive targets for drug design. In this review, we summarize data on aza-peptide bond chemistry, with implications for the improvement of aza-peptide chemical synthesis.

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Section: Continued On the Next Pagementioning

confidence: 99%

Aza-peptides: expectations and reality

Arujõe¹,

Järv²,

Mastitski³

et al. 2022

PEAS

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“…Therefore, it seemed desirable to develop greener and milder methods for the 2,6-diamino-4-arylpyridine-3,5-carbonitrile. Green chemistry approaches are most important due to the reduction in byproducts, a reduction in produced waste, and reduction of energy cost [41][42][43][44][45][46][47][48].…”

Section: Introductionmentioning

confidence: 99%

One-Pot-Multicomponent Synthesis of 2,6-Diamino-4-arylpyridine-3,5-dicarbonitrile Derivatives Using Nanomagnetic Fe3O4@SiO2@ZnCl2

et al. 2018

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Nanomagnetic Fe3O4@SiO2@ZnCl2 was used as a simple, cost-effective, and reusable heterogeneous catalyst for the synthesis of 2,6-diamino-4-arylpyridine-3,5-dicarbonitriles by a one-pot-three-component condensation reaction of malononitrile, ammonium acetate, and aldehydes under solvent-free conditions at 110 °C. Simple and mild reaction conditions, facile preparation of the catalyst, the use of a cheap catalyst and easy workup and isolation are notable features of this method. ABSTRAKNanomagnetik Fe3O4@SiO2@ZnCl2 digunakan sebagai katalis sederhana, hemat biaya, dan merupakan katalis heterogen yang dapat digunakan kembali untuk sintesis 2,6-diamino-4-arilpiridin-3,5-dikarbonitril melalui reaksi kondensasi tiga komponen one-pot antara malononitril, amonium asetat, dan aldehida dengan kondisi tanpa pelarut pada temperatur 110 °C. Kondisi reaksi yang sederhana dan ringan, persiapan katalis yang mudah, penggunaan katalis yang murah dan mudah dilakukan serta mudah diisolasi adalah aspek yang penting dari metode ini.

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“…Several synthetic methods have been proposed and used to prepare these aza-amino acid precursors [1][2][3][4][5][6][7][8][9][10][11][12]. The most frequently used synthetic route for the preparation of N-protected alkyl-and arylhydrazines is 2.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of aza-phenylalanine, aza-tyrosine, and aza-tryptophan precursors via hydrazine alkylation

Mastitski¹,

Haljasorg²,

Kipper³

et al. 2015

Proc. Estonian Acad. Sci.

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Aza-amino acid precursors with an aromatic side chain were synthesized using hydrazine alkylation. This synthetic pathway avoided use of hydrogen gas and expensive hydrogenation catalysts. For the optimization of this alkylation reaction various solvents and different reaction conditions were used. Aza-phenylalanine, aza-tyrosine, and aza-tryptophan precursors with different N-and side-chain protecting groups were synthesized starting from N-protected hydrazines.

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One-Pot Synthesis of Fmoc- and Boc-Protected Aza-Methionine Precursors from 2-Methylthioacetaldehyde Dimethyl Acetal

Cited by 10 publications

References 10 publications

Aza-peptides: expectations and reality

Aza-peptides: expectations and reality

One-Pot-Multicomponent Synthesis of 2,6-Diamino-4-arylpyridine-3,5-dicarbonitrile Derivatives Using Nanomagnetic Fe<sub>3</sub>O<sub>4</sub>@SiO<sub>2</sub>@ZnCl<sub>2</sub>

Synthesis of aza-phenylalanine, aza-tyrosine, and aza-tryptophan precursors via hydrazine alkylation

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