A Simple and Efficient Approach for the Synthesis of 1, 3‐Oxazolidines from β‐Amino Alcohols Using Grinding Technique. Issue 48 (21st December 2018)

• Record Type: Journal Article
• Authors: Singh, Nasseb; Dar, Alamgir A.; Kumar, Anil
• Is Part Of: ChemistrySelect. Volume 3:Issue 48(2018)
• Page Start: 13675
• Page End: 13681
• Publication Date: 2018-12-21
• Subjects: Benzotriazole -- 5-Membered -- 1, 3-Oxazolidine -- Heterocycles -- Mechanical Grinding; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201802369
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: An environment‐friendly and efficient method for synthesis of 1, 3‐oxazolidines from β‐amino alcohols has been developed using paraformaldehyde in the presence of 10 mol% alkali as a green reaction medium. The method is concise, simple, transition metal free, and high yielding at room temperature with wide substrate scope and functional group compatibility. The optimized method can be used for the synthesis of 1, 3‐oxazolidines intermediates, which are used as prodrug moieties to improve therapeutic potential of the parent drug. Structure and formation of the synthesized compounds has been characterized and confirmed through conventional spectroscopic techniques, such as 1 H nuclear magnetic resonance (NMR), 13 C NMR, and mass spectroscopy. Abstract : An eco‐friendly synthesis of benzotriazolated 1, 3‐oxazolidines from β‐amino alcohols using paraformaldehyde and 10 mol% NaOH has been carried. The process bears a broad substrate scope and functional group compatibility which can be used to generate 1, 3‐oxazolidines and other useful moieties as a result of their potential to act as effective prodrugs. Application of mechanical grinding for the quantitative formation of desired products, cost‐effectiveness, time‐economy, transition metal free catalysis etc. are the prominent features of the protocol.