By Kolio D. Troev
Chemistry and alertness of H-Phosphonates is a wonderful resource for these making plans the synthesis of latest phosphorus-containing compounds and specifically derivatives containing a phosphonate, phosphoramide or phosphonic acid diester team. the wealthy chemistry, reasonably-priced and straightforward availability of diesters of H-phosphonic acid makes them a good selection as synthone in a couple of essentially very important reactions.Phosphonic acid esters are intermediates within the synthesis of significant periods of compounds akin to alpha-aminophosphonic acids, bisphosphonates, epoxyalkylphosphonates, alpha-hydroxyalkylphosphonates, phosphoramides, poly(alkylene H-phosphonate)s, poly(alkylene phosphate)s, nucleoside H-phosphonates. The synthesis of every of those compound periods is reviewed in detail.Alpha-Aminophosphonic acids are a tremendous type of biologically lively compounds, that have got an expanding volume of awareness simply because they're thought of to be structural analogues of the corresponding Alpha-amino acids. The utilities of alpha-aminophosphonates as peptide mimics, haptens of catalytic antibodies, enzyme inhibitors, inhibitors of cancers, tumours, viruses, antibiotics and pharmacologic brokers are good documented. Alpha-Hydroxyalkanephosphonates are compounds of vital organic and medicinal functions. Dialkyl epoxyalkylphosphonates are of curiosity as a result of their use as intermediates within the synthesis of bioactive elements, and as modifiers of ordinary and artificial polymers. Bisphosphonates are medicinal drugs which were primary in several bone ailments, and feature lately been used effectively opposed to many parasites. Poly(alkylene H-phosphonate)s and poly(alkylene phosphate)s are promising, biodegradable, water soluble, new polymer-carriers of substances. Nucleoside H-phosphonates appear to be the main appealing applicants as beginning fabrics within the chemical synthesis of DNA and RNA fragments. The 5'-hydrogen phosphonate-3'-azido-2',3'-dideoxythimidine is among the most important anti-HIV prodrug, that is at present in scientific trials.
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Additional info for Chemistry and Application of H-Phosphonates
The rate of the reaction appears to be strongly dependent on the strength of the base. Triethylamine was only slightly more effective as a catalyst than tributylamine or triamylamine, but was 1000 times more effective than pyridine . When the Atherton–Todd reaction is carried out in the presence of carboxylic acids, the formation of phosphate products is observed . Et3N/CCl4 (RO)2P(O)H + R1C(O)OH (RO)2P(O)OC(O)R1 Amino acids were phosphorylated successfully using Atherton–Todd reaction conditions [89,90].
1). This pathway includes alkylation of the amine and formation of a monoalkyl H-phosphonate salt. 7 6/14/2006 4:16 PM Page 43 Characteristic Reactions of P-H Group 43 RO X _ + O NR'3 P RO O RO P H OR + NR'3 O H RO P _ + O NR'3 H R This monoalkyl H-phosphonate anion is the actual base, which then deprotonates the dialkyl H-phosphonate. It has been established that alkylammonium or metal salts, containing monoalkyl H-phosphonate anions, promote the Atherton–Todd reaction . Taking into account the observation of Kong and Engel that the Atherton–Todd reaction does not take place in the absence of a base, these results indicate that the monoalkyl Hphosphonate anion is playing a key role as an intermediate in the amine-promoted Atherton–Todd reaction.
7 6/14/2006 4:16 PM Page 57 Characteristic Reactions of P-H Group 57 _ O t-BuOK / t-BuOH (EtO)2 P(O)H + Ph2 C CRNO2 Ph2C DMSO CRN-OP(O)(OEt)2 - (EtO)2PO2 Ph2C CR N _ O _ (EtO)2PO2 P(O)(OEt)2 Ph2C CRN _ O _ - (EtO)2PO2 P(O)(OEt)2 R _ (EtO)2PO R Ph2C Ph2C N NH II I Under similar conditions, the thiosubstituted alkene (R ϭ SCMe3) yielded only the intermediate azirine II. When the above addition reaction was carried out in the presence of potassium tert-butoxide, addition of the phosphorus nucleophile to the benzylidene carbon atom takes place .
Chemistry and Application of H-Phosphonates by Kolio D. Troev