Application of phosphonyl carbanions to highly regioselective synthesis of some diazaphospholes and pyrazolinyl phosphonates

Abdou, Wafaa M.; Khidre, Maha D.; Khidre, Rizk E.

doi:10.1016/j.ejmech.2008.03.032

Cited by 34 publications

(17 citation statements)

References 15 publications

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“…2‐Diazo‐1,3‐indandione 134 was treated with a little excess of molar amount of methyl 135a or ethyl phosphonoacetate 135b in a mixture of LiOH/H 2 O/CHCl 3 at the reflux temperature to give pyrazolinyl phosphonate 136 (~27% yield) and diazaphosphole 137 (~44% yield) (Scheme ). These compounds were found to possess antibacterial and antifungal activities .…”

Section: Synthetic Methodsmentioning

confidence: 99%

Synthetic Routes to Pyrazole‐3(5)‐carboxylates

Khidre

Abdel‐Wahab

Farahat

et al. 2015

Journal of Heterocyclic Chem

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Section: Synthetic Methodsmentioning

confidence: 99%

Synthetic Routes to Pyrazole‐3(5)‐carboxylates

Khidre

Abdel‐Wahab

Farahat

et al. 2015

Journal of Heterocyclic Chem

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“…We now report on multicomponent reactions with three or more reactants combined in a one‐pot procedure to give a single product. Accordingly, efficient synthesis of α ‐aminophosphonates from selected amine, aldehyde, and phosphorus reagents including trialkylphosphites, dialkylphosphites, or hexaalkyl triamidophosphites could be achieved following the previously reported method using 10% FeCl 3 in tetrahydrofuran (THF) solution to facilitate the Mannich‐type reaction of aldehyde, amine, and phosphorus reagent.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Various Schiff Bases Containing Isoxazole Ring and Their Applications with Thioglycollic Acid and Diverse Phosphorus Reagents

Shady

Abu-Bakr

Khidre

2015

Journal of Heterocyclic Chem

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A series of Schiff bases bearing isoxazole and pyrazole rings were synthesized. Application of thioglycollic acid on two selective synthesized Schiff bases afforded the corresponding thiazolidin‐4‐one derivatives. On the other hand, following the multicomponents one‐pot Kabachnik– Fields reaction, the Schiff base generated in situ from 4‐chlorobenzaldehyde and 5‐methyl isoxazol‐3‐amine was trapped by phosphorus reagents to produce the corresponding amino phosphonates in moderate yields. However, the latter products could also be obtained in better yields (≥78%) by directly applying the dialkylphosphites to a selective synthesized Schiff base. Similarly, a series of α‐aminophosphonates could be obtained from 5‐chloro‐3‐methyl‐1H‐pyrazol‐4‐carbaldehyde, 5‐methylisoxazol‐3‐amine, and phosphorus reagents. Moreover, applying hexaalkyl triamido phosphites to the N‐(4‐chlorobenzylidene)‐5‐methylisoxazol‐3‐amine in ethanol afforded methylphosphonic diamide derivatives, whereas N‐((5‐chloro‐3‐methyl‐1H‐pyrazol‐4‐yl)methylene)‐5‐methylisoxazol‐3‐amine underwent dechlorination through reaction with hexaalkyl triamido phosphites to give the respective amine derivatives.

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“…Although a variety of synthetic methods of α‐aminophosphonates are available, approaches to enaminophosphonates are somewhat even less known. In connection with our interest in preparation of β‐enamino‐ and α‐aminophosphonates 5–11, we have recently reported a strategy for the synthesis of a series of these compounds. The latter arose from one‐pot three‐component synthesis, via Kabachnik–Fields reaction, starting from substituted amines, aldehydes, and tri‐/dialkyl phosphites, in the presence of tetrahydrofuran (THF)–FeCl 3 (10%) solution 12.…”

Section: Introductionmentioning

confidence: 99%

Carbodiimides in the Synthesis of Enamino‐ and α‐Aminophosphonates as Peptidomimetics of Analgesic/Antiinflammatory and Anticancer Agents

Abdou

Barghash

Bekheit

2012

Archiv der Pharmazie

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Carbodiimide that was generated from the condensation reaction of iminophosphorane with phenylisocyanate was allowed to react with different phosphorus nucleophiles. Thus, the in situ resulted heterocumulene reacted with dialkylhydrogenphosphonates in tetrahydrofuran (THF)/FeCl(3) /H(2) O system to give fused pyrrole- (≈14%) and pyrimidinephosphonates (≈57%). On the other hand, with tris-(dialkyl)aminophosphines, the reaction afforded the corresponding hexaalkylphosphinic diamides as a water-sensitive fine powder, quite stable for a few days in a desiccator. When a protonating agent was present in the reaction medium, the reaction was markedly accelerated leading to the formation of the phosphamides. Next, some saturated and unsaturated Horner-Emmons reagents were applied in situ to the same carbodiimide to obtain more phosphorylated N-heterocycles. The analgesic and antiinflammatory activities of the newly synthesized compounds were investigated and showed significant activities. Finally, we further estimated the antitumor activity of five new phosphonates against four carcinoma cell lines.

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Application of phosphonyl carbanions to highly regioselective synthesis of some diazaphospholes and pyrazolinyl phosphonates

Cited by 34 publications

References 15 publications

Synthetic Routes to Pyrazole‐3(5)‐carboxylates

Synthetic Routes to Pyrazole‐3(5)‐carboxylates

Synthesis of Various Schiff Bases Containing Isoxazole Ring and Their Applications with Thioglycollic Acid and Diverse Phosphorus Reagents

Carbodiimides in the Synthesis of Enamino‐ and α‐Aminophosphonates as Peptidomimetics of Analgesic/Antiinflammatory and Anticancer Agents

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