Iodine-Catalyzed, Efficient Synthesis of α-Hydroxy Phosphonates in Water

Wang, Hongshe; Zeng, June

doi:10.1080/10426500903061541

Cited by 6 publications

(3 citation statements)

References 27 publications

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“…The drawback of this protocol is the rather complicated work-up comprising quenching, extraction, and then chromatography. An interesting finding is that iodine may also be a catalyst in the reaction of aldehydes and triethyl phosphite ( Table 2 /Entry 9) [ 49 ]. The catalytic effect of I 2 was explained similarly as that of the acid catalysts: iodine is able to interact with the oxygen atom of the carbonyl group, making the C=O bond more electrophilic.…”

Section: Synthetic Routes Towards α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids.

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Section: Synthetic Routes Towards α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

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“…Alternatively, in some circumstances, extremely acidic conditions are applied, also incompatible with DNA . Only rare studies reported a process conducted in aqueous media under thermal conditions. , …”

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“…33 Only rare studies reported a process conducted in aqueous media under thermal conditions. 34,35 Hence, we turned our focus on the investigation of these potentially valuable on-DNA Abramov and Pudovik reactions, even though known reaction conditions may be detrimental to DNA's integrity, 36 in the hope that a judicious choice of reaction conditions could transcend such obstacles. After examining commonly exploited off-DNA reaction conditions, we determined that basic aqueous reaction media could be particularly appropriated.…”

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Constructive On-DNA Abramov Reaction and Pudovik Reaction for DEL Synthesis

Sun

Xiao

Chen

et al. 2023

ACS Med. Chem. Lett.

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Organophosphonic compounds are distinctive among natural products in terms of stability and mimicry. Numerous synthetic organophosphonic compounds, including pamidronic acid, fosmidromycin, and zoledronic acid, are approved drugs. DNA encoded library technology (DELT) is a wellestablished platform for identifying small molecule recognition to target protein of interest (POI). Therefore, it is imperative to create an efficient procedure for the on-DNA synthesis of α-hydroxy phosphonates for DEL builds.

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Unusual Reactivity of Aryl Aldehydes with Triethyl Phosphite and Zinc Bromide: A Facile Preparation of Epoxides, Benzisoxazoles, and α‐Hydroxy Phosphonate Esters

et al. 2015

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A facile preparation of trans‐epoxides was achieved by a (EtO)3P–ZnBr2‐mediated deoxygenation reaction of the corresponding 2‐nitrobenzaldehydes. The sterically hindered analogues of 2‐nitrobenzaldehyde underwent a reaction with triethyl phosphite in the presence of ZnBr2 as the catalyst to form benzisoxazoles as the sole product. Under identical conditions, the reactions of electron‐rich as well as moderately electron‐deficient aryl aldehydes furnished the corresponding α‐hydroxy phosphonate esters.

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Iodine-Catalyzed, Efficient Synthesis of α-Hydroxy Phosphonates in Water

Cited by 6 publications

References 27 publications

Synthesis and Reactions of α-Hydroxyphosphonates

Synthesis and Reactions of α-Hydroxyphosphonates

Constructive On-DNA Abramov Reaction and Pudovik Reaction for DEL Synthesis

Unusual Reactivity of Aryl Aldehydes with Triethyl Phosphite and Zinc Bromide: A Facile Preparation of Epoxides, Benzisoxazoles, and α‐Hydroxy Phosphonate Esters

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