4264-27-1

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 199277-23-1 1-azido-2-(phenylethynyl)benzene 
• 70-11-1 α-bromoacetophenone 
• 3453-00-7 diethyl benzoylmethylphosphonate 
• 948-65-2 2-phenyl-indole 
• 1022-46-4 2-phenyl-4H-3,1-benzoxazin-4-one 
• 122-52-1 triethyl phosphite 
• 15341-31-8 α-nitro-stilbene 

Relevant academic research and scientific papers

Palladium-Catalyzed Oxidative Cyclization for the Synthesis of Indolyl/Pyrrolyl 3-Phosphonates

Imino-/enaminophosphonates derived from amines and diethyl phenacyl phosphonates undergo oxidative cyclization via C H bond activation catalyzed by palladium chloride to provide a convenient route for the synthesis of substituted indol-3-yl and pyrrol-3-yl phosphonates. (Figure presented.) .

Method for synthesizing indole-3-phosphonate

The invention discloses a method for synthesizing indole-3-phosphonate. 2-alkynyl trinitride and phosphonate are used as raw materials, and reaction is performed under the effects of a gold catalyst and a solvent to prepare the indole-3-phosphonate. The reaction temperature is 30-80 DEG C, the reaction time is 0.5-24 hours, the using amount of the catalyst is 0.5-5% of the total mole percent of the raw materials, and the mole ratio of the 2-alkynyl trinitride to the phosphonate is 1:10 to 1:20. The method is simple and convenient to operate and good in adaptability, the product is high in yield, the catalyst is easily separated from the product, the post-treatment is simple, and a process is green and environmentally friendly.

An expedient synthesis of pyrrole-2-phosphonates via direct oxidative phosphorylation and γ-hydroxy-γ-butyrolactams from pyrroles

An expedient oxidative phosphorylation of pyrroles has been disclosed. The reaction of dialkyl phosphite and pyrrole in the presence of AgNO 3/K2S2O8 in DMF/H2O (8:1) produced pyrrole-2-phosphonates in good yields. In the absence of dialkyl phosphite, γ-hydroxy-γ-butyrolactam derivative was formed as a major product.

Direct oxidative C-P bond formation of indoles with dialkyl phosphites

The direct phosphonation of indoles was developed. In this reaction, dialkyl phosphites and indoles were used as substrates, and the C-P bond was formed through oxidative coupling mediated by silver(I) acetate. Various indoles and different dialkyl phosphites were effective substrates for the reaction, and dialkylphosphoryl-substituted indoles were obtained in up to 71% yield. Georg Thieme Verlag Stuttgart · New York.

Phosphono-Substituted Isoindolines and Indoles from 2,3- and 2,4-Benzoxazin-1-ones

Reactions of 2,3-benzoxazinone 1 and 2,4-benzoxazinone 2, with trialkyl phosphites 3a-c provide access to new phosphono-substituted isoindolines 6a-f and indoles 19a-e, respectively. Phosphonosubstituted 2,3-benzoxazines 5a-c were also obtained in the first reaction. Bisisoindolinylidene (7) was, however, isolated in low yields when 1 was heated with triethyl or triisopropyl phosphite at 100°C whereas at 170°C 7 was obtained as the major product (～53%). On the other hand, the reaction of 1 or 2 with dialkyl phosphonates 4a-c proceeded in the presence of aqueous solution of NaOH (5%) to give the respective alkylated product 14a-c or 20a-c.

Reactions of Ethyl phosphites with β-Nitrostyrenes. The Role of Nitrosoalkenes as Intermediates

3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150 deg C while reaction with (EtO)2PO(1-)/(Et2O)P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type aducts are postulated as intermediates.Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150 deg C or (EtO)2PO(1-)/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nucleophile at the benzylidene carbonatom.Evidence for the formation of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO(1-)/(EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P.The Michael-type adducts PhCHCH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100 deg C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85percent H2SO4 of the adducts of PhCH=C(R)NO2 with (EtO)2PO(1-) (R = Me) or (EtO)3P (R = Ph).