Synthesis of potential drugs based on hydrophosphoryl compounds. IV. Synthesis and antifungal activity of unsaturated organophosphorus compounds

Yudelevich, V. I.; Belakhov, V. V.; Belyaeva, T. N.; Sergienko, L. V.; Komarov, E. V.; Ионин, Б. И.; Mikhailova, Margarita; Araviiskii, R. A.

doi:10.1007/bf00765969

Cited by 4 publications

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“…Polycyclic compounds incorporating a P-heterocyclic moiety are of special importance due to their optoelectronic properties and applications [24][25][26]. Moreover, a few biologically active 5-membered P-heterocyclic derivatives are also known, which showed promising antitumor [27][28][29][30], antifungal [31,32] or GABA receptor antagonist activity [33].…”

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Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

Bagi¹,

Herbay²,

Péczka³

et al. 2020

Beilstein J. Org. Chem.

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A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3-phospholene oxides in methanesulfonic acid, or via the formation of cyclic chlorophosphonium salts. Whereas mixtures of the 2- and 3-phospholene oxides formed, when the isomerization of 3-phospholene oxides was attempted under thermal conditions, or in the presence of a base. The mechanisms of the various double bond migration pathways were elucidated by quantum chemical calculations.

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confidence: 99%

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

Bagi¹,

Herbay²,

Péczka³

et al. 2020

Beilstein J. Org. Chem.

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“…[7,8] Oxaphospholenes 3-4,f ive-membered heterocycles containing one double bond,o ne oxygen and one phosphorusa tom, could be useful precursorsf or furanose carbohydrate mimics, [9] while the saturated oxaphospholanes 5 are bioisosteres of g-butyrolactones. [11] On the other hand, bactericidal, [12] insecticidal, [12] pesticidal, [12] herbicidal [13] and fungistatic [14] properties have been attributed to several benzoxaphospholes and phospholene oxides. [10] Parthenolide 6 is an example of an a-methylene-g-butyrolactone being evaluated as apotential anticancer treatment.…”

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confidence: 99%

“…[10] Parthenolide 6 is an example of an a-methylene-g-butyrolactone being evaluated as apotential anticancer treatment. [11] On the other hand, bactericidal, [12] insecticidal, [12] pesticidal, [12] herbicidal [13] and fungistatic [14] properties have been attributed to several benzoxaphospholes and phospholene oxides.…”

Section: Introductionmentioning

confidence: 99%

Fifty Years of (Benz)oxaphospholene Chemistry

Berton

Heugebaert

Virieux

et al. 2017

Chemistry A European J

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The first synthesis of benzoxaphospholenes dates back to the 1960s. Since then,t he structuralv ariety of reported (benz)oxaphospholenesh as steadily increased. Organophosphorusc ompounds have caught the interesto fs ynthetic chemists for ac ouple of decades now because of their interesting biological properties. Oxaphospholenes,i n particular,c ould serve as carbohydrate mimetics, and benzoxaphospholenes have been reported to possess bactericidal, insecticidal, herbicidal, and fungistatical properties. Transesterification reactions and addition of phosphorus nucleophiles to carbonylc ompoundsw ere reaction types that led to the production of the first (benz)oxaphospholenes.When it was discovered that allenylphosphonates could easily be obtainedf rom propargyl alcohols and dialkylh alophosphites, the electrophile-induced cyclization reaction of these allenylphosphonate precursors resulted in ah uge boom in the amounto fr eports on oxaphospholene synthesis. To this day,t his methodi ss till frequently used. Ring-closing metathesis and Horner-Wadsworth-Emmons reactions have also provent heir potentialf or the preparation of oxaphospholenes. In recent years, Pd, Rh and Au-catalysis have made their entry,g enerating (benz)oxaphospholenes from a wide variety of simple substrates. Ac ouple of miscellaneous methods are summarized at the end of the Review.[a] J.

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