EMAIL THIS PAGE TO A FRIEND

Chemical & pharmaceutical bulletin

Synthesis of heterocyclic compounds through palladium-catalyzed C-H cyclization processes.


PMID 24088691

Abstract

Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

373192
Palladium, evaporation slug, diam. × L 0.9 cm × 1.2 cm, 99.95% trace metals basis
Pd
373206
Palladium, evaporation slug, diam. × L 0.6 cm × 0.6 cm, 99.95% trace metals basis
Pd
348678
Palladium, foil, thickness 1.0 mm, 99.9% trace metals basis
Pd
287474
Palladium, foil, thickness 0.5 mm, 99.9% trace metals basis
Pd
348643
Palladium, foil, thickness 0.25 mm, 99.98% trace metals basis
Pd
411450
Palladium, foil, thickness 0.05 mm, 99.9% trace metals basis
Pd
267120
Palladium, foil, thickness 0.025 mm, 99.9% trace metals basis
Pd
203998
Palladium, granular, 99.99% trace metals basis
Pd
203939
Palladium, powder, 99.999% trace metals basis
Pd
464651
Palladium, powder, <75 μm, 99.9% trace metals basis
Pd
326666
Palladium, powder, <1 μm, ≥99.9% trace metals basis
Pd
346985
Palladium, rod, diam. 6.25 mm, ≥99.9% trace metals basis
Pd
267082
Palladium, sponge, 99.9% trace metals basis
Pd
267112
Palladium, wire, diam. 1.0 mm, 99.9% trace metals basis
Pd
348694
Palladium, wire, diam. 0.5 mm, 99.9% trace metals basis
Pd
643181
Palladium, extent of labeling: 5 wt. % loading (dry basis), matrix activated carbon, wet support, Degussa type E105CA/W
Pd
686468
Palladium, nanopowder, <25 nm particle size (TEM), ≥99.5%
Pd
GF46569831
Palladium, foil, 6mm disks, thickness 0.025mm, as rolled, 99.99+%
Pd
GF29399158
Palladium, foil, 6mm disks, thickness 0.25mm, as rolled, 99.95%
Pd
GF21228825
Palladium, foil, 8mm disks, thickness 0.025mm, as rolled, 99.99+%
Pd
GF79862833
Palladium, wire reel, 0.05m, diameter 1.0mm, as drawn, 99.99+%
Pd
GF22660264
Palladium, wire reel, 0.1m, diameter 0.5mm, as drawn, 99.95%
Pd
GF00436733
Palladium, wire reel, 0.5m, diameter 1.0mm, as drawn, 99.99+%
Pd
GF85707513
Palladium, wire reel, 0.5m, diameter 1.0mm, hard, 99.95%
Pd
GF76572940
Palladium, wire reel, 1m, diameter 0.025mm, as drawn, 99.9%
Pd
GF96794409
Palladium, wire reel, 25m, diameter 0.125mm, hard, 99.95%
Pd
GF58966037
Palladium, wire reel, 2m, diameter 0.5mm, as drawn, 99.95%
Pd
GF24288790
Palladium, wire reel, 5m, diameter 0.25mm, hard, 99.95%
Pd
GF02178761
Palladium, wire reel, 2m, diameter 0.025mm, as drawn, 99.9%
Pd
GF93105547
Palladium, wire reel, 2m, diameter 0.02mm, as drawn, 99.95%
Pd