Syntheses of Heterocycle-2,3-Fused Indoline and Azaindoline ­Derivatives

Abstract

We describe a practical method for synthesizing heterocycle-2,3-fused indoline or azaindoline derivatives through haloetherification and cyclization. We applied this method in syntheses of six- to eight-membered heterocycle-2,3-fused indoline and azaindoline derivatives. These derivatives, which contain sp3-hybridized carbons, might be useful as new scaffolds in medicinal chemistry.

Syntheses of Oxazolidinone-2,3-Fused Indoline and Azaindoline Derivatives

“…We also reported a practical synthetic method for the construction of six- to eight-membered heterocycle-2,3-fused indoline and azaindoline derivatives. 4 Herein, we report the design and syntheses of oxazolidinone-2,3-fused indoline and azaindoline derivatives 2 via one-pot cyclization with isocyanate 3 (Scheme 1 ).…”

Fluorinated 2,6-Xylenesulfonyl Group: A Protective Group for Amines

“…Nosyl groups are stable under acidic or basic conditions and can be cleaved by treatment with soft nucleophiles such as thiolates via the formation of Meisenheimer complexes. Nosyl groups have been used in the synthesis of polyfunctional nitrogen-containing molecules, including pharmaceuticals and natural products . One of the weaknesses of the nosyl group is lability toward reducing agents or organometallic species .…”