The Synthesis of Benzhydroximoyl Chloride and Nitrile Oxides under Solvent Free Conditions

Abstract

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More Sustainable Approaches for the Synthesis of N-Based Heterocycles

“…The formation of the oxide species is facilitated by the presence of an oxime and NCS in the reaction medium (Scheme ). − By use of an alkene as dipolarophile, this method proved also to be efficient in the preparation of isoxazolines . Recently, a one-pot procedure was reported for this reaction in which the reaction between Oxone, acidic silica gel, and an aldoxime at room temperature for 13 min led to the formation of halogenated aldoxime and is further reacted with triethylamine and styrene for 2 min …”

“…188 Recently, a onepot procedure was reported for this reaction in which the reaction between Oxone, acidic silica gel, and an aldoxime at room temperature for 13 min led to the formation of halogenated aldoxime and is further reacted with triethylamine and styrene for 2 min. 190 Through the combined use of one-pot Knoevenagel and Michael reactions between rhodanines, aromatic aldehydes and ammonium N-aryl-dithiocarbamates, the dithioesters formed can be cyclized to furnish thiazolo-1,3-dithiins, -thiazines, or -oxathiins depending on the inorganic species used (Scheme 27). For the annulation of formed dithioesters, montmorillonite K-10 clay, modified Li + -montmorillonite clay, and molecular iodine were used to yield different families of compounds under microwave irradiation (77-89% yield).…”

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

“…As described in 2007 by Bigdeli, Mahdavinia, and Jafari, 3,5-disubstituted 2-isoxazolines can be successively obtained using 1,3-DP cycloaddition of Y-C 6 H 4 CNO to styrene in solvent-free conditions and using the one-pot procedure— Scheme 50 [ 55 ]. Interestingly, reaction mixture ingredients (oxime, oxone, styrene, silica gel, and Et 3 N) were ground together within 15 min and finally extracted.…”

“… One-pot preparation of 3,5-disubstituted 2-isoxazolines via Y-C 6 H 4 CNO 1,3-DP cycloaddition to styrene [ 55 ]. Ar = Y-C 6 H 4 when Y = H, p -Cl, p -Me, p -O 2 N, and others; a = OXONE, silica-gel, Et 3 N, grinding together, 15 min, rt; 90–92% yield.…”