Use of 5-deoxy-ribo-hexofuranose derivatives for the preparation of 5'-nucleotide phosphonates and homoribonucleosides

1989 ◽  
Vol 54 (4) ◽  
pp. 1055-1066 ◽  
Author(s):  
Sergei N. Mikhailov ◽  
Nelly Sh. Padyukova ◽  
Marat Ya. Karpeiskii ◽  
Lidiya I. Kolobushkina ◽  
Leon N. Beigelman
Keyword(s):  
Triethyl Phosphite ◽  
Arbuzov Reaction ◽  
Trimethylsilyl Derivatives ◽  
The Arbuzov Reaction ◽  
General Method

A convenient and general method is proposed for the synthesis of 5'-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose which can easily be produced in preparative quantities from D-glucose. Phosphonate IIIe was synthesized by means of the Arbuzov reaction between 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose and triethyl phosphite. The consecutive acetolysis, condensation with uracil and N6-benzoyladenine bis-trimethylsilyl derivatives and deblocking possessed phosphonate analogs of 5'-nucleotides in good yields. The intermediate 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose derivatives were used for the preparation of homonucleosides.

The arbuzov reaction of triethyl phosphite with elemental iodine

1980 ◽  
Vol 21 (3) ◽  
pp. 321-322 ◽  
Author(s):  
A. Skowrońska ◽  
M. Pakulski ◽  
J. Michalski ◽  
D. Cooper ◽  
S. Trippett
Keyword(s):  
Triethyl Phosphite ◽  
Arbuzov Reaction ◽  
The Arbuzov Reaction ◽  
Elemental Iodine

ChemInform Abstract: THE ARBUZOV REACTION OF TRIETHYL PHOSPHITE WITH ELEMENTAL IODINE

1980 ◽  
Vol 11 (17) ◽  
Author(s):  
A. SKOWRONSKA ◽  
M. PAKULSKI ◽  
J. MICHALSKI ◽  
D. COOPER ◽  
S. TRIPPETT
Keyword(s):  
Triethyl Phosphite ◽  
Arbuzov Reaction ◽  
The Arbuzov Reaction ◽  
Elemental Iodine

Synthesis of Phosphonates via Michaelis-Arbuzov Reaction

2017 ◽  
Vol 14 (6) ◽  
pp. 883-903 ◽  
Author(s):  
Boppudi Hari Babu ◽  
Gandavaram Syam Prasad ◽  
Chamarthi Naga Raju ◽  
Mandava Venkata Basaveswara Rao
Keyword(s):  
Reaction Times ◽  
Biologically Active ◽  
Fine Tuning ◽  
Arbuzov Reaction ◽  
Reaction Conditions ◽  
Solvent Type ◽  
Potential Applications ◽  
Synthetic Methodologies ◽  
Optimal Reaction ◽  
The Arbuzov Reaction

Background: Michaelis–Arbuzov reaction has played a key role for the synthesis of dialkyl or diaryl phosphonates by reacting various alkyl or aryl halides with trialkyl or triaryl phosphite. This reaction is very versatile in the formation of P-C bond from the reaction of aliphatic halides with phosphinites or phosphites to yield phosphonates, phosphinates, phosphine oxides. The Arbuzov reaction developed some methodologies, possible mechanistic pathways, selectivity, potential applications and biologically active various phosphonates. Objective: The synthesis of phosphonates via Michaelis–Arbuzov reaction with many new and fascinating methodologies were developed and disclosed in the literature, and these are explored in this review. Conclusion: This review has discussed past developments and vast potential applications of Arbuzov reaction in the synthesis of organophosphonates. As presented in this review, various synthetic methodologies were developed to prepare a large variety of phosphonates. Improvements in the reaction conditions of Lewis-acid mediated Arbuzov rearrangement as well as the development of MW-assisted Arbuzov rearrangement were discussed. Finally, to achieve high selectivities and yields, fine-tuning of reaction conditions including solvent type, temperature, and optimal reaction times to be considered.

Microwave irradiation and catalysis in organophosphorus reactions

2019 ◽  
Vol 91 (1) ◽  
pp. 145-157 ◽  
Author(s):  
György Keglevich ◽  
Nóra Zsuzsa Kiss ◽  
Réka Henyecz ◽  
Zoltán Mucsi
Keyword(s):  
Microwave Irradiation ◽  
Aryl Halides ◽  
Arbuzov Reaction ◽  
Phosphine Oxides ◽  
Direct Esterification ◽  
Phosphinic Acids ◽  
Mw Irradiation ◽  
Organophosphorus Chemistry ◽  
Active Methylene ◽  
The Arbuzov Reaction

AbstractThe usual advantage of microwave (MW) assistance is making organic reactions faster and more efficient. In this article we present reaction types from organophosphorus chemistry, when MW-assisted transformations (e.g. the direct esterification and alkylating esterification of phosphinic acids) may be promoted by suitable catalysts, or vice versa, when a catalytic reaction is enhanced by MW irradiation (e.g. the Arbuzov reaction of aryl halides), and when catalysts may be omitted or simplified under MW irradiation as shown by the alkylation of active methylene containing P=O substrates/the Kabachnik–Fields reaction/deoxygenation of phosphine oxides, and the Hirao reaction, respectively.

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