Triflic Anhydride-Mediated Unprecedented Reactivities of Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access to γ-Butenolides and Oxazoles

Herein, we present two unprecedented reactions for the synthesis of γ-butenolides and oxazoles, leveraging Tf<sub>2</sub>O's promoted reactivity of nitriles with diacetonide endoglucofuranose and 1,2,3,5-tetra-<i>O</i>-acetyl-β-d-ribofuranose. This method is highly efficient and straightforward and employs a one-step, metal-free protocol. It is effective with both aromatic and aliphatic nitriles and demonstrates a broad substrate scope. Our approach provides a versatile and practical pathway for the synthesis of structurally diverse compounds, significantly expanding the utility of Tf<sub>2</sub>O in synthetic chemistry.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-05
DOI
https://doi.org/10.1021/acs.joc.4c01423
Citations
2
Primary Topic
Advanced Synthetic Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.50

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article

Triflic Anhydride-Mediated Unprecedented Reactivities of Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access to γ-Butenolides and Oxazoles

Norein Sakander, Tariq Ahmad Dar, Qazi Naveed Ahmed
2 citations
The Journal of Organic Chemistry
Advanced Synthetic Organic Chemistry
0.50
article

Triflic Anhydride-Mediated Unprecedented Reactivities of Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access to γ-Butenolides and Oxazoles

Norein Sakander, Tariq Ahmad Dar, Qazi Naveed Ahmed
article en
2 citations

Abstract

Herein, we present two unprecedented reactions for the synthesis of γ-butenolides and oxazoles, leveraging Tf<sub>2</sub>O's promoted reactivity of nitriles with diacetonide endoglucofuranose and 1,2,3,5-tetra-<i>O</i>-acetyl-β-d-ribofuranose. This method is highly efficient and straightforward and employs a one-step, metal-free protocol. It is effective with both aromatic and aliphatic nitriles and demonstrates a broad substrate scope. Our approach provides a versatile and practical pathway for the synthesis of structurally diverse compounds, significantly expanding the utility of Tf<sub>2</sub>O in synthetic chemistry.

The Journal of Organic ChemistryVol. 89(18)
Indian Institute of Integrative Medicine (IN), Academy of Scientific and Innovative Research (IN)
Council of Scientific and Industrial Research, India, Science and Engineering Research Board
Openalex Percentile: Top 40%
Advanced Synthetic Organic Chemistry
0.50
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Triflic Anhydride-Mediated Unprecedented Reactivities of Diacetonide Endoglucofuranose and Ribose Tetracetate: Direct Access to γ-Butenolides and Oxazoles — Norein Sakander, Tariq Ahmad Dar, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS