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

Autor: Sakander N; Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Dar TA; Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India., Ahmed QN; Natural Product and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Jammu 180001, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2024 Sep 20; Vol. 89 (18), pp. 13308-13318. Date of Electronic Publication: 2024 Sep 05.
DOI: 10.1021/acs.joc.4c01423
Abstrakt: Herein, we present two unprecedented reactions for the synthesis of γ-butenolides and oxazoles, leveraging Tf 2 O's promoted reactivity of nitriles with diacetonide endoglucofuranose and 1,2,3,5-tetra- O -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 2 O in synthetic chemistry.
Databáze: MEDLINE