A Convenient Synthesis and Herbicidal Activity ofN-phosphonoalkylpyrazolo[4,3-e][1,2,4]-triazolo[1,5-d]pyrimidines

Xiao, Linxia; Li, Ke; Shi, Dashuang

doi:10.1080/10426500802070270

Cited by 17 publications

(10 citation statements)

References 12 publications

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“…The latter's constitute important motifs in medicinal chemistry [23][24][25][26][27] due to their structural similarities of 21 to α-amino acids 20.…”

Section: Reactions With Iminesmentioning

confidence: 99%

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Abdou

Barghash

Bekheit

2015

Synthetic Communications

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In this study, we report recent investigations of the chemical reactivity of alkyl phosphites mainly trialkyl and dialkyl phosphites with molecules containing different nitrogen-containing compounds reported by us and other research groups over the last twenty five years. Earlier leader important reports were also considered. The reviewed investigations in this article are customized, only according to the type of the nitrogenfunctional groups: [amines (primary, secondary, and tertiary amines), imines, amides, thioamides, nitriles, isocyanates, isothiocyanates, oximes, hydrazones, diazo, and azides]and not according to the site of attack or the final products. Furthermore, the present review article focuses on the synthesis of α-amino-, β-amino-and/or enaminophosphonates. These compounds occupy an important role in pharmaceutical chemistry.2 GRAPHICAL ABSTRACT:

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“…The latter's constitute important motifs in medicinal chemistry [23][24][25][26][27] due to their structural similarities of 21 to α-amino acids 20.…”

Section: Reactions With Iminesmentioning

confidence: 99%

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Abdou

Barghash

Bekheit

2015

Synthetic Communications

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“…Generally, these organophosphorus compounds have high biological efficiency, metabolic stability, and low toxicity in mammalian cells [2]. In fact, α-aminophosphonates have introduced many of medicinal benefits, possess antifungal [2], herbicidal [4], antibacterial [5,6] and antiviral [7] properties, and can function as enzyme inhibitors [8,9] and anticancer agents [10,11]. As a result, they become tremendously essential in medical and agricultural chemistry.…”

Section: Introductionmentioning

confidence: 99%

Facile Synthesis of Iron-Based MOFs MIL-100(Fe) as Heterogeneous Catalyst in Kabachnick Reaction

et al. 2021

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An effective technique was proposed for the synthesis of novel α-aminophosphonates: a three-component one-pot condensation reaction of aniline, aromatic aldehydes, and triphenyl phosphite in the presence of (MIL-100(Fe)) as a heterogeneous catalyst. Initially, MIL-100(Fe) was synthesized using H3BTC and ferric nitrate at low temperature and atmospheric pressure. Further, MIL-100(Fe) was characterized using various techniques such as XRD, BET surface area, scanning electron microscopy (SEM), Fourier-transform infrared (FT-IR), and thermogravimetric analysis (TGA). Herein, MIL-100(Fe) showed exceptional catalytic performance for the synthesis of α-aminophosphonate and its derivatives compared with conventional solid catalysts, and even homogeneous catalysts. The study demonstrated that MIL-100(Fe) is an ecofriendly and easily recyclable heterogeneous catalyst in Kabachnick reactions for α-aminophosphonate synthesis, with high yield (98%) and turnover frequency (TOF ~ 3.60 min−1) at room temperature and a short reaction time (30 min).

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“…The replacement of flat carboxylic moiety with either the phosphonyl, phosphinyl, or phosphinoyl group in the structure of α-amino acids enables them to have extremely valuable biological properties. These compounds are strong bioregulators and are used in agrochemicals as growth regulators, fungicides, and insecticides; they show antiviral, antibacterial, and anticancer properties [1,2,3,6,9,11,12,13].…”

Section: Introductionmentioning

confidence: 99%

Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles

et al. 2019

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In this study, Michaelis-Arbuzov-type reaction of 1-imidoalkyltriarylphosphonium salts with phosphites, phosphonites, and phosphinites was used in the synthesis of a wide range of phosphorus analogs of α-amino acids such as 1-imidoalkylphosphonates, 1-imidoalkylphosphinates, and 1-imidoalkylphosphine oxides. Large differences were observed in the reactivity of substrates depending on their structure, especially on the type of phosphonium moiety and N-protecting group. The conditions under which the expected products can be obtained in good to excellent yields have been developed. Mechanistic aspects of the transformation have been provided.

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A Convenient Synthesis and Herbicidal Activity ofN-phosphonoalkylpyrazolo[4,3-e][1,2,4]-triazolo[1,5-d]pyrimidines

Cited by 17 publications

References 12 publications

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Facile Synthesis of Iron-Based MOFs MIL-100(Fe) as Heterogeneous Catalyst in Kabachnick Reaction

Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles

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