24391-84-2

Upstream product

• 111079-46-0 3-iodo-1H-pyridin-2-one 
• 536-74-3 phenylacetylene 
• 124-41-4 sodium methylate 
• 431942-30-2 5-bromo-2-phenylfuro[2,3-b]pyridine 
• 113975-22-7 2-fluoro-3-iodopyridine 
• 933768-06-0 2-phenyloxepino[2,3-b]pyridine 
• 207602-10-6 2-fluoro-3-[(trimethylsilyl)ethynyl]pyridine 
• 100-52-7 benzaldehyde 
• 94446-97-6 2-bromo-3-bromomethylpyridine 
• 131747-54-1 (2-bromopyrid-3-yl)methanol 
• 35905-85-2 2-bromonicotinic acid 
• 111079-46-0 3-iodo-2-hydroxypyridine 
• 108-86-1 bromobenzene 
• 13466-35-8 3-chloro-2-hydroxypyridine 

Relevant academic research and scientific papers

Rhodium-Catalyzed Direct Arylation of Furopyridine: Synthesis and the Cardiac Effects of Dictamnine Derivatives

Herein is reported a Rh2(OAc)4/IMes ? HCl system that promotes the chemoselective installation of aryl groups at the 2-position of furo[2,3-b]pyridine (53–94% yields). The method is applicable to the direct modification of the natura

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.

Tandem Sonogashira-Hagihara coupling/cycloisomerization reactions of ethynylboronic acid MIDA ester to afford 2-heterocyclic boronic acid MIDA esters: A concise route to benzofurans, indoles, furopyridines and pyrrolopyridines

A one-pot process that provides direct access to 2-heterocyclic MIDA (N-methyliminodiacetic acid) boronates has been developed. The reaction of 2-iodophenols or 2-iodoanilines with ethynylboronic acid MIDA ester readily afforded 2-substituted heterocyclic compounds. Amidine and phosphazene bases, especially TMG (1,1,3,3-tetramethylguanidine) assumed an important role in the tandem Sonogashira-Hagihara coupling/cycloisomerization reactions.

Access to functionalized thienopyridines via a reagent-capsule-assisted coupling, thiolation and cyclization cascade sequence

Thienopyridines and related heterocycles were prepared in a straightforward manner in moderate to good yields and under mild conditions by palladium-catalysed cross-coupling of ortho-fluorinated iodopyridines and terminal alkynes, followed by a reagent-capsule-assisted thiolation cyclization process. By applying paraffin wax capsules to prevent catalyst poisoning and undesired side reactions, the separation and purification processes were reduced.

Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO

The synthesis of 2-substituted indoles and benzofurans was achieved by nucleophilic aromatic substitution, followed by subsequent 5-endo-dig cyclization between the nucleophile and an ortho acetylene. The acetylene serves the dual role of the electron withdrawing group to activate the substrate for SNAr, and the C1-C2 carbon scaffold for the newly formed 5-membered heteroaromatic ring. This method allows for the bond forming sequence of Ar-X-N/O-C1 to proceed in a single synthetic step, furnishing indoles and benzofurans in moderate to high yields. Since the method is not transition metal mediated, brominated and chlorinated substrates are tolerated, and benzofuran formation can be conducted using water or water-DMSO mixtures as solvent. This journal is

Copper- And ligand-free heteroannulation of o-halohydroxypyridine with terminal alkynes using Pd/C catalyst: One-pot synthesis of 2-substituted furopyridines and their functionalization

Three types of isomeric 2-substituted furo[3,2-b]pyridine, furo[2,3-b]pyridine and furo[3,2-c]pyridine were prepared using Pd/C-catalyzed heteroannulation of o-halopyridinols and terminal alkynes under copperand ligand-free conditions. We also demonstrated that double functionalization yielding 2,3-disubstituted furopyridines could be achieved through heteroannulation followed by bromination and Suzuki/Heck reactions. In addition, the use of recoverable Pd/C in the absence of a cocatalyst and ligand can aid in the development of greener chemical processes.

One-pot synthesis of 2-substituted benzo[b]furans via Pd-tetraphosphine catalyzed coupling of 2-halophenols with alkynes

A catalyst composed of [Pd(η3-C3H 5)Cl]2 and N,N,N',N'-tetra(diphenylphosphinomethyl) pyridine-2,6-diamine (L) was found to be effective for one-pot synthesis of 2-substituted benzo[b]furans from 2-halophenols and alkynes. For 2-bromo-3-hydroxypyridine, the catalyst loading could be as low as 1 ppm and the turnover number (TON) was up to 870000. the Partner Organisations 2014.

Pd2dba3/Bippyphos: A robust catalyst system for the hydroxylation of aryl halides with broad substrate scope

A mixture of tris(dibenzylideneacetone)dipalladium(0) (Pd 2dba3) and 5-(di-tert-butylphosphino)-1′,3′, 5′-triphenyl-1′H-[1,4′]bipyrazole (Bippyphos) is shown to be a robust and efficient catalyst system for the hydroxylation of structurally diverse (hetero)aryl halides under mild conditions and with broad substrate scope. Included in this reactivity survey is the successful synthesis of substituted benzofurans and related heteroatomic derivatives, which are formed via the hydroxylation of 2-haloalkynylarenes. Notably, a significant number of the reactions reported herein proceed at room temperature, and we have demonstrated that it is possible to conduct reactions on the benchtop under air using unpurified solvents with negligible loss in reactivity versus related transformations conducted under inert atmosphere conditions. We also report herein the first crystallographically characterized (Bippyphos)Pd(II) complex, which confirms the ability of this synthetically useful ligand to adopt a bidentate binding motif in a manner similar to Buchwald's biarylphosphine ligand class. Copyright

Synthesis of melatonin analogues derived from furo[2,3-b]- and [2,3-c]pyridines by use of a palladium-copper catalyst system

2,3,5-Substituted furo[2,3-b]pyridine was synthesised by palladium-catalyzed reaction of 5-bromo-2-hydroxy-3-iodopyridine and phenylacetylene with (Ph3P)2PdCl2, CuI in Et3N. A carbonylative cyclization of 5-hydroxy-2-methoxy-4-(2-phenylethynyl)pyridine with carbon monoxide in methanol with PdCl2, CuCl2 under basic conditions, has been accomplished to prepare methyl 2,5-substituted furo[2,3-c]pyridine-3-carboxylate.

CONDENSED HETEROAROMATIC RING SYSTEMS. VII. SYNTHESIS OF THIENOPYRIDINES, THIENOPYRIMIDINES, AND FUROPYRIDINES FROM o-SUBSTITUTED N-HETEROARYLACETYLENES

The cross-coupling reaction of 2-chloro-3-iodo- and 4-chloro-3iodopyridines with phenylacetylene in the presence of dichlorobis(triphenylphosphine)palladium occured at the 3-position.The 3-ethynylpyridines containing an adjacent chloro group were converti