Synthesis of Some Novel Bisisoxazolidine Derivatives from Glyoxal‐derived Bisnitrones via Simultaneous Double Cycloaddition Reactions in Water

Abstract

Simultaneous double 1,3‐dipolar cycloaddition reactions of glyoxal‐derived bisnitrones have been described in water. Significant rate acceleration and improved yields of exclusively diastereoselective and regioselective bisisoxazolidines in water have been observed at room temperature in a short reaction time compared with conventional solvents.

Synthesis of Some Novel Class of Bis(isoxazoline) and Bis(aziridine) Derivatives

“…1,3‐Dipolar cycloaddition reactions are an integral and weighty part of organic chemistry in pedagogy and research as well. The wealthy literature on cycloaddition reactions of nitrones for the synthesis of isoxazolidine and isoxazoline derivatives and their further applications have been widely illustrated while synthesis of bis(isoxazolidine) and bis(isoxazoline) derivatives is challenging and needs to be explored especially because conversions of these derivatives to aziridines via Baldwin rearrangement are found to have vast synthetic potential in this chemistry . The chemistry of three‐membered ring heterocycles, especially aziridines, has attracted the attention of synthetic chemists for more than a century because of its ability of acting as versatile species in organic synthesis .…”

Synthesis of Some New Scaffolds of Amino Isoxazolidines and Their Further Functionalization into New Class of Peptides: A New Approach

“…N‐ methylhydroxylamine was purchased from Aldrich Chemical Company (Lancaster, UK) and was used as received. N ‐phenylhydroxylamine was prepared following standard methods available in literature and has been used in various reported synthesis .…”

“…In continuation of our efforts to synthesize new organic molecules using green methodologies via nitrone cycloaddition reactions , herein, we wish to report synthesis of new scaffolds of amino isoxazolidine derivatives and their further functionalization into a new class of peptide molecules (Schemes and ).…”

Synthesis of Some Novel Class of Regioselective Spiro Isoxazolidine Derivatives via 1,3‐Dipolar Cycloaddition Reaction of N‐Benzyl‐C‐fluoro‐substituted Phenyl Nitrones in Ionic Liquid

“…Isoxazolidines are also found to exhibit medicinal activities such as antibacterial, anticonvulsant, antibiotic, antituberculer, and antifungal activity . As a part of our ongoing research program to develop new methodologies for the synthesis of new molecules , herein, we report regioselective synthesis of some new spiro isoxazolidine derivatives ( 3 ) using N‐ benzyl‐ C‐ fluoro‐substituted phenyl nitrones ( 1 ) with α‐ N ‐substituted furan derivatives ( 2 ) via 1,3‐dipolar cycloaddition reaction in good to excellent yields in ionic liquid (Scheme , Table ). Furthermore, these regioselective spiro isoxazolidine derivatives are found to have vast synthetic potential as they could be converted into synthetically more important new spiro 1,3‐amino alcohols ( 4 ).…”