A kinetic study of the hydrolysis of crystal violet and some terminal and bridged analogues

Synthesis and Spectroscopic Properties of Rosamines with Cyclic Amine Substituents

“…White solid (308 mg, 93%). 1 H NMR (500 MHz, CDCl 3 ) δ 8.14 (d, 2H, J ) 9.0 Hz), 6.86 (dd, 2H, J ) 9.0, 2.4 Hz), 6.67 (d, 2H, J ) 2.4 Hz), 3.86 (t, 8H, J ) 4.9 Hz), 3.33 (t, 8H, J ) 4.9 Hz); 13 C NMR (125 MHz, CDCl 3 ) δ 175.1, 158.0, 155.3, 127.7, 114.1, 111.2, 100.0, 66.5, 47.5. MS (ESI) m/z calcd for (M + H) + C 21 H 23 N 2 O 4 367.17; found 367.17.…”

“…White solid (680 mg, 60%). 1 H NMR (500 MHz, CDCl 3 ) δ 8.13 (d, 2H, J ) 9.0 Hz), 6.86 (dd, 2H, J ) 9.0, 2.3 Hz), 6.66 (d, 2H, J ) 2.3 Hz), 3.59 (t, 8H, J ) 5.2 Hz), 3.37 (t, 8H, J ) 5.2 Hz), 1.47 (s, 18H); 13 3,6-Dipyrrolidin-1-yl-xanthen-9-one (10). Yellow solid (90 mg, 18%).…”

“…Yellow solid (90 mg, 18%). 1 H NMR (500 MHz, CDCl 3 ) δ 8.08 (d, 2H, J ) 8.9 Hz), 6.50 (dd, 2H, J ) 8.9, 2.2 Hz), 6.28 (d, 2H, J ) 2.2 Hz), 3.34 (t, 8H, J ) 6.6 Hz), 2.01 (t, 8H, J ) 6.6 Hz); 13 General Procedure for the Synthesis of Rosamine Derivatives. A Grignard reagent or lithium reagent (1.0 mmol) was added dropwise over 1 min to the solution of 3,6-diamino-xanthen-9-one (0.2 mmol) in 5 mL of THF at 0 °C.…”

“…Other work deals with modification of the 2-carboxylate group of rhodamines (not shown), , but the parent systems are also made via condensation reactions at elevated temperatures. An alternative approach to syntheses of rosamine dyes is to add an organo-lithium or -magnesium compound to the carbonyl group of a xanthone and then protonate to cause loss of water and generate the product . That approach has been applied extensively by Detty and co-workers to make rosamines (and especially S-, Se-, and Te - analogs), − for their photodynamic and other medicinal properties. − Similarly, attack of aryl Grignards on solid-supported xanthones F was used in a supported parallel synthesis approach to a library of rosamine derivatives G (Figure b) …”

Fluorescent Amino- and Thiopyronin Dyes

“…The starting material for this transformation is a known compound that we prepared via a slight modification of the literature procedure (see the Supporting Information); this modification was scalable to at least 13 g since, unlike the original method, no chromatography was required. Amines related to 1a and 1b have been prepared via condensation procedures that involve several steps; – the reaction outlined below is more direct once the common ditriflyl xanthone starting material has been made. The product precipitates from the reaction mixture after addition of water and is then recrystallized.…”