The first regio- and diastereoselective synthesis of homochiral perhydroimidazoisoxazoles via the 1,3-dipolar cycloaddition of imidazoline 3-oxides with (1S)-(−)-β-pinene

Synthesis and Ring Opening Reactions of Tetrahydroimidazo[1,5- b ][1,2,4]oxadiazol-2(1 H )-thiones

“…Taylor and Francis shall not be liable for any losses, actions, claims, proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or howsoever caused arising directly or indirectly in connection with, in relation to or arising out of the use of the Content. 7 We have shown the 1,3-dipolar cycloaddition reactions of cyclic nitrones 1 with dipolarophiles as arylisocyanates, 8,9 styrene, 10 DMAD, 11,12 and β-pinene 13 to proceed regio and in the case of chiral nitrones diastereoselectively. 1 1,3-Dipolar cycloadditions of nitrones with variety of dipolarophiles take an important place among the methods for the synthesis of five membered heterocyclic compounds.…”

“…3-Methyl-3a-phenyl-5-p-tolyl-tetrahydroimidazo [1,5-b] [1,2,4] 13 heated at 50 • C on a water bath for 25 h. The solvent was removed and the residue extracted with dichloromethane (3 × 15 mL). The combined extracts were dried over anhydrous Na 2 SO 4 , filtered, and the solvent removed under vacuum.…”

“…6 The reaction of acyclic nitrones with isothiocyanates was shown to give mainly oxadiazolidin-5-thiones. 7 We have shown the 1,3-dipolar cycloaddition reactions of cyclic nitrones 1 with dipolarophiles as arylisocyanates, 8−9 styrene, 10 DMAD, 11−12 and β-pinene 13 to proceed regio-and, in the case of chiral nitrones, diastereoselectively. When heated, the adducts from isocyanates and styrene undergo retro 1,3-dipolar cycloaddition, while the adducts from DMAD and β-pinene give the corresponding imidazoles.…”

ZnO NPs: an efficient and reusable nanocatalyst for the synthesis of nitrones from DAG using H2O as a solvent at room-temperature

“…A number of reports have appeared on the chemistry of 1,3-dipolar species, with special emphasis on their cycloaddition reaction with multiple bonds [14]. The cycloadducts of di-and triarylimidazoline 3-oxides [15] with a variety of dipolarophiles [16][17][18][19][20][21] give interesting biologically active heterocyclic compounds. 1 The 1,3-dipolar cycloaddition of imidazolin 3-oxides was shown to proceed regio-and diasteroselectivity and interesting reactions of these adducts under various conditions such as the double cis elimination they undergo in the presence of dialkylamines was reported [22,23].…”

A green synthesis of nitrones from diamino glyoxime using aldehydes and ketones

“…A number of reports have appeared on the chemistry of 1,3-dipolar species, with special emphasis on their cycloaddition reaction with multiple bonds [14]. The cycloadducts of di-and tri-arylimidazoline-3-oxides [15] with a variety of dipolarophiles [16][17][18][19][20][21] give interesting biologically active heterocyclic compounds [22]. The 1, 3-dipolar cycloaddition of imidazolin-3-oxides was shown to proceed regio-and diasteroselectivity and interesting reactions of these adducts under various conditions such as the double cis elimination they undergo in the presence of dialkylamines was reported [23,24].…”