O-Mesitylenesulfonylhydroxylamine and Related Compounds - Powerful Aminating Reagents

2-Alkoxycarbonylcycloimmonium ylides, efficient 1,4-dipole equivalents in the synthesis of new conjugated betaines.

“…4,11,12 Synthesis of 4a and 5a. To a stirred suspension of 0.63 g of the pyridinium salt la (2 mmo1) and 1.10 g of K2C03 (8 rnmo1) in dry acetonitri1e (10 mI), 0.24 mI of pheny1 isocyanate (2.2 rnmo1) were added, and the reaction mixture was súrred at room temperature for 20 h. Then, the inorganic residue was filtered off and the liquid was concentrated to dryness.…”

Simple Molecules, Highly Efficient Amination

“…Tamura has reported the synthesis of O -mesitylsulfonylhydroxylamine (MSH; 1 ; Figure 1.1 ) and related compounds and has examined their reactions with various nucleophiles in detail [1] . With regard to the formation of C − N bonds by the use of MSH, however, the applicable carbanions were quite limited -to stabilized enolates only -and the product yields of the resulting amines were quite low.…”

“…was purifi ed by fl ash column chromatography, with elution with 50% ethyl acetate/ hexane, to afford 4 -benzoyloxymorpholine ( 11 , 7.71 g, 37 mmol, 74%) of > 95% purity by 1 …”

“…NaOH and the amino components were extracted with CH 2 Cl 2 (10 mL × 3). The organic fraction was washed with brine (10 mL), dried over Na 2 SO 4 , and concentrated in vacuo to afford 4 -phenylmorpholine as a white solid (80 mg, 0.49 mmol, 98%) of > 95% purity by 1 …”

Cycloaddition Reactions of 1-Aza- and 1,3-Diazaazulenium 1-Methylides

“…Heteroaromatic N-ylides [1][2][3] and heteroaromatic N-imines [4][5][6][7][8] , which are highly useful synthetic intermediate for the construction of fused heterocycles via 1,3-dipolar cycloaddition reaction. 9,10 We previously reported about the synthesis and reactions of 1-azaazulene N-imine (1) where interesting dipolar cycloadditions were observed.…”