Catalytic Direct Regioselective Synthesis of Phosphonylated Tetrazoles from Aryl Diazonium Salts and Seyferth-Gilbert Reagent

Zhai, Shi‐Jing; Peng, Xing; Zhang, Fa‐Guang; Ma, Jun‐An

doi:10.1021/acs.orglett.9b03800

Cited by 35 publications

(22 citation statements)

References 61 publications

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“…Very recently, Ma et al . reported an interesting approach to fix phosphonate moiety on the chiral amino acid scaffold by employing a Ag‐catalyzed [3+2] cycloaddition reaction between aryl diazonium salts and Seyferth–Gilbert reagent (Scheme 42c) [95] . 4‐NH 2 ‐Phenylalanine was smoothly converted into the diazonium salt and then cycloadded with Seyferth–Gilbert reagent with exclusive regioselectivity, thus furnishing the tetrazole‐linked phosphono‐amino ester 115 .…”

Section: Asymmetric Construction Of Amino Acid Phosphonate Derivativesmentioning

confidence: 99%

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

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Chiral amino acids featuring a phosphonate pendant arm are an important type of biologically active scaffold. Here in this review, we comprehensively summarize the modern synthetic methods towards asymmetric construction of chiral amino carboxylic‐phosphonic acid derivatives. The main streams of such interesting compounds include phosphono‐containing α‐, β‐, and γ‐amino acid derivatives, amino acid fluorophosphonate derivatives, amino acid cyclopropanylphosphonate derivatives, and bisphosphono‐amino acid derivatives. Chiral resolution protocols, chiral auxiliary‐directed syntheses, and valorization of the pool of abundant chiral amino acid resources remain contemporary concerns, and meanwhile catalytic enantioselective synthesis has also emerged as a potent strategy as demonstrated by the latest advances.magnified image

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Section: Asymmetric Construction Of Amino Acid Phosphonate Derivativesmentioning

confidence: 99%

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Cahard

Cao

et al. 2020

Adv Synth Catal

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“…[36] However, the direct utilization of diazomethylphosphonate reagents with arenediazonium dipolarophiles wasn't reported until recently, when Ma and coworkers disclosed a novel silver-catalyzed [3 + 2] cycloaddition reaction of Seyferth-Gilbert reagent 1 with arenediazonium salts 37 to obtain phosphonylated tetrazoles 38 (Scheme 25). [37] Moreover, the same group also reported the facile synthesis of phosphonyltriazines 40 via a silver-catalyzed [3 + 3] annulation involving glycine imino esters 39 and Seyferth-Gilbert reagent 1 (Scheme 26). [38]…”

Section: Synthesis Of Other Heterocyclesmentioning

confidence: 99%

“…However, the direct utilization of diazomethylphosphonate reagents with arenediazonium dipolarophiles wasn‘t reported until recently, when Ma and co‐workers disclosed a novel silver‐catalyzed [3+2] cycloaddition reaction of Seyferth‐Gilbert reagent 1 with arenediazonium salts 37 to obtain phosphonylated tetrazoles 38 (Scheme 25). [37] …”

Section: Synthesis Of Other Heterocyclesmentioning

confidence: 99%

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Jamali

Vaishanv

Mohanan

2020

The Chemical Record

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Azaheterocycles are one of the most prevalent classes of compounds present in numerous bioactive compounds, natural products, and agrochemicals, and undoubtedly, new methods to access them are always in high demand. Among the methods available, the 1,3dipolar cycloaddition reactions involving diazo compounds are particularly attractive because of their ability to rapidly construct densely functionalized azaheterocycles in a regioselective manner. In this context, the Bestmann-Ohira reagent has become a well-known reagent for the 1,3dipolar cycloaddition reactions to produce phosphonylated heterocycles, besides its widespread use as a homologating agent for the conversion of aldehydes to alkynes. This account details our efforts toward broadening the synthetic utility of the Bestmann-Ohira reagent and related compounds for the preparation of azaheterocycles such as pyrazoles, spirooxindoles, triazoles, triazolines, and spiropyrazolines, emphasizing on domino multicomponent reactions employing readily available feedstock reagents.

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“…Further studies indicated that 3‐bromophthalides, 3‐formylchromones and aryldiazonium salts could couple with SGR to furnish phosphorylated pyrazoles and tetrazoles.…”

Section: Reactions Involving Heterocyclic Ring Formationmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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Catalytic Direct Regioselective Synthesis of Phosphonylated Tetrazoles from Aryl Diazonium Salts and Seyferth-Gilbert Reagent

Cited by 35 publications

References 61 publications

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

Asymmetric Synthesis of Chiral Amino Carboxylic‐Phosphonic Acid Derivatives

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

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