ChemInform Abstract: Direct Synthesis of Organic Azides from Alcohols Using 2‐Azido‐1,3‐dimethylimidazolinium Hexafluorophosphate.

Kitamura, Masaya; Koga, Tatsuya; Yano, Masakazu; Okauchi, Tatsuo

doi:10.1002/chin.201238054

Cited by 2 publications

(4 citation statements)

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“…However, use of unstable and explosive trifluoromethanesulfonyl azide (TfN 3 ) was a problem. Recently, safer diazotransfer reagents, ADMP [24,25] and Goddart-Borger reagent (1) [26][27][28], appeared and can be used instead of TfN 3 . [29], which was recently demonstrated in the model study in total synthesis of cortistatin A 4 and J 5 by Yamashita and Hirama's group (Scheme 5) [30].…”

Section: Preparation Of Organic Azidesmentioning

confidence: 99%

“…Direct conversion method without Mitsunobu conditions was also published (eq 7) [23]. Recently, Kitamura and co-workers demonstrated that the safer and more stable azido compound ADMP (2-azido-1,3dimethylimidazolinium hexafluorophosphate) was a good azidation reagent [24,25]. Azides can be prepared from primary amines by way of diazoniumion formation followed by nucleophilic azidations (eq 8).…”

Section: Preparation Of Organic Azidesmentioning

confidence: 99%

“…However, use of unstable and explosive trifluoromethanesulfonyl azide (TfN 3 ) was a problem. Recently, safer diazotransfer reagents, ADMP [24,25] and Goddart-Borger reagent (1) [26][27][28], appeared and can be used instead of TfN 3 . 1,4-Azidation has also been reported in the total syntheses of marine bisindole alkaloids hamacanthin A (11), B (12) and the antipodode of cis-dihydrohamacanthin B (13) by Kawasaki et al…”

Section: Preparation Of Organic Azidesmentioning

confidence: 99%

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Recent Applications and Developments of Organic Azides in Total Synthesis of Natural Products

Tanimoto

Kakiuchi

2013

Natural Product Communications

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Organic azides have been exploited since their discovery because of their high reactivities. Various organic reactions using azides have been synthetically applied in chemical biology, pharmaceuticals, medicinal, and agricultural areas. In this review, we present some recent applications and developments of organic azides in the total synthesis of natural products (mostly within five years), especially alkaloids. We focus not only on application examples of organic azides, but also show their preparation methods including recently reported procedures concerning their decomposing and reducing methods in the syntheses of bioactive molecules.

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Section: Preparation Of Organic Azidesmentioning

confidence: 99%

Section: Preparation Of Organic Azidesmentioning

confidence: 99%

“…However, use of unstable and explosive trifluoromethanesulfonyl azide (TfN 3 ) was a problem. Recently, safer diazotransfer reagents, ADMP [24,25] and Goddart-Borger reagent (1) [26][27][28], appeared and can be used instead of TfN 3 . 1,4-Azidation has also been reported in the total syntheses of marine bisindole alkaloids hamacanthin A (11), B (12) and the antipodode of cis-dihydrohamacanthin B (13) by Kawasaki et al…”

Section: Preparation Of Organic Azidesmentioning

confidence: 99%

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Recent Applications and Developments of Organic Azides in Total Synthesis of Natural Products

Tanimoto

Kakiuchi

2013

Natural Product Communications

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“…Hence there was increase in demand for stable and safer alternative. To sort out the problems of toxicity and instability, 2-azido-1,3-dimethylimidazolinium chloride (ADMC) and its related hexafluorophosphate were explored [15][16].…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis of MgO Nanoparticles Using Caesalpinia Sappan Seeds and their Application for Direct Conversion of Alcohol to Azide

Lalithamba

Divyarani

Sreenivasa

et al. 2022

jmmf

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Azides have been considered as one of the energy rich functional groups as they are prominent precursors for reactive species like nitrenes and nitrenium ions. Also, they were utilized in synthesis of triazoles, triazolines and triazenes. The present work reports an eco- friendly synthesis of MgO NPs by utilizing Caesalpinia Sappan seeds as a novel fuel by solution combustion method. Multiple characterization techniques encompassing FTIR, UV- visible, XRD and SEM were used to study physico-chemical properties of synthesized MgO NPs. A convenient synthesis of amino alcohol via mixed anhydride method was carried out in the first step. Further, amino alkyl azide has been synthesized under mild condition by using the green synthesized MgO nanoparticles as a catalyst along with the addition of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate, a safe, stable and efficient diazo transfer reagent. Structures of newly synthesized compounds were well characterized by HRMS, Proton and C-13 analysis techniques.

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ChemInform Abstract: Direct Synthesis of Organic Azides from Alcohols Using 2‐Azido‐1,3‐dimethylimidazolinium Hexafluorophosphate.

Cited by 2 publications

References 1 publication

Recent Applications and Developments of Organic Azides in Total Synthesis of Natural Products

Recent Applications and Developments of Organic Azides in Total Synthesis of Natural Products

Green Synthesis of MgO Nanoparticles Using Caesalpinia Sappan Seeds and their Application for Direct Conversion of Alcohol to Azide

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