Phospha-fluorescein (POF), a phosphine oxide-containing analogue of fluorescein, was synthesized and its photophysical properties were examined. Compared with fluorescein and sila-fluorescein, POF displayed significantly red-shifted absorption and fluorescence as well as superior photobleaching resistance, while retaining the pH-responsive characteristics of fluorescein dyes.

1,2-cis-Ribofuranosides are stereoselectively synthesized in high yields directly from 1-hydroxy sugars and alcohols or trimethylsilylated nucleophiles by the use of diphosphonium salts as a condensation reagent.

In the presence of a catalytic amount of [(R)-1,1′-bi-2-naphthalenediolato(2-)-O,O′]oxotitanium, silyl enol ethers of thioesters reacted with α,β-unsaturated ketones to afford the corresponding Michael adducts (1,5-dicarbonyl compounds) in high yields with moderate to high enantiomeric excesses.

A series of 1,2-dihydro-5-imidazo[1,2-a]pyridinyl-2(1H)-pyridonones was synthesized and evaluated for positive inotropic activity, 1,2-Dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2- oxo-3-pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1,2-a]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increase in the i.v. cardiotonic potency (ED50) from 52 to 23 micrograms/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1,2-dihydro-5-(6-fluoroimidazo[1,2-a] pyridin-2-yl)-6-methyl-2(1H)-pyridinone (3u) was the most potent (i.v. ED50 11 micrograms/kg) in this series. E-1020 is presently under development for the treatment of congestive heart failure.

In the presence of a catalyst generated from GaCl3 and a silver salt (AgClO4 or AgSbF6), the Friedel-Crafts acylation reaction of aromatic compounds such as anisole and veratrole with acid anhydrides smoothly proceeds to afford the corresponding aromatic ketones in high yields.