An efficient method for the synthesis of spiro and fused N-heterocyclic phosphor esters. Reactions of triketoindan-2-oxime with α-phosphonyl carbanions

Abdou, Wafaa M.; Sediek, Ashraf A.; Khidre, Maha D.

doi:10.1007/s00706-007-0806-z

Cited by 20 publications

(13 citation statements)

References 22 publications

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“…Furthermore, 4H-isooxazol-4-ylphosphonate was formed via [1 ? 4] cycloaddition mechanism from the reaction of triketoindan-2-oxime with phosphorus reagents [25]. In support of the formation of the intermediates 3, the 31 P NMR spectrum was recorded in an early stage of the reaction for the crude mixture of trimethyl phosphite and azide 1.…”

Section: Resultsmentioning

confidence: 99%

Spiro- and substituted tetrahydrobenzo[b]thiophene-triazaphospholes and phosphoramidates as potent antineoplastic agents: synthesis, biological evaluation, and SAR studies

2015

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New and efficient conjugate addition reaction of trimethyl, triethyl, and triisopropyl phosphites with 2-azido-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile was developed and furnished spiro-triazaphosphole-oxide derivatives in &70 % yield. Contrary to these results, linear substituted phosphoramidates were obtained from the reaction of the azide with dimethyl, diethyl, and diisopropyl phosphites.N-Alkylaminoor 2-aminotetrahydrobenzo[b]thiophene-3-carbonitrile was also isolated in *10 % yield from the previous two reactions. In the context of this work, hexaalkylphosphorus triamides were caused to react with the same substrate afforded the corresponding phosphoric triamides only in the presence of a protonating agent (dil. alcohol). The three reactions proceeded smoothly, cleanly, and were completed within *6 h at r.t. Pharmacological evaluation results of antibreast, anticolon, and antiprostate carcinoma cell lines properties for the products were discussed in terms of structure-activity relationship to define a chromophore for lead compounds. Graphical abstract

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Section: Resultsmentioning

confidence: 99%

Spiro- and substituted tetrahydrobenzo[b]thiophene-triazaphospholes and phosphoramidates as potent antineoplastic agents: synthesis, biological evaluation, and SAR studies

2015

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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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“…As a part of our continued interest in the development of convenient synthetic approaches to β-enamino- and α-aminophosphonates with anti-inflammatory properties [13–20], we recently successfully synthesized a series of mono- and bisphosphonate-based tetrazolo[1,5- a ]quinolines with marked anti-inflammatory properties [21–22]. Following this, synthesis of the target compounds, substituted tetrazolo[1,5- b ]pyridazinphosphor esters, is described herein.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and quantitative structure–activity relationship study of substituted imidazophosphor ester based tetrazolo[1,5-b]pyridazines as antinociceptive/anti-inflammatory agents

Abdou

Ganoub²,

Sabry³

2013

Beilstein J. Org. Chem.

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SummaryA high-yielding general synthesis of imidazophosphor ester based tetrazolo[1,5-b]pyridazines is described. A conjugated reaction between 3,6-diazidopyridazine and different types of phosphonyl carbanion reagents followed by intramolecular cyclization afforded the target products, by using sodium ethanolate solution as a reaction medium. Among the products, five compounds, at a dose of 50 mg per kilogram body weight, showed a notable antinociceptive and anti-inflammatory activity without toxic side-effects.

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An efficient method for the synthesis of spiro and fused N-heterocyclic phosphor esters. Reactions of triketoindan-2-oxime with α-phosphonyl carbanions

Cited by 20 publications

References 22 publications

Spiro- and substituted tetrahydrobenzo[b]thiophene-triazaphospholes and phosphoramidates as potent antineoplastic agents: synthesis, biological evaluation, and SAR studies

Spiro- and substituted tetrahydrobenzo[b]thiophene-triazaphospholes and phosphoramidates as potent antineoplastic agents: synthesis, biological evaluation, and SAR studies

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

Synthesis and quantitative structure–activity relationship study of substituted imidazophosphor ester based tetrazolo[1,5-b]pyridazines as antinociceptive/anti-inflammatory agents

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