63581-47-5

Upstream product

• 452-58-4 2,3-Diaminopyridine 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-09-4 4-methoxybenzoic acid 
• 63581-34-0 2-amino-3-(p-methoxybenzylideneamino)pyridine 
• 4214-75-9 2-amino-3-nitropyridine 
• 273-21-2 imidazo[4,5-b]pyridine 
• 696-62-8 para-iodoanisole 
• 1428156-21-1 3-((2-methoxyethoxy)methyl)-3H-imidazo[4,5-b]pyridine 
• 1428156-35-7 3-((2-methoxyethoxy)methyl)-2-(4-methoxyphenyl)-3H-imidazo[4,5-b]pyridine 
• 100-07-2 4-methoxy-benzoyl chloride 

Relevant academic research and scientific papers

Regioselective C2-arylation of imidazo[4,5-b]pyridines

We show that N3-MEM-protected imidazo[4,5-b]pyridines undergo efficient C2-functionalisation via direct C-H arylation. Twenty-two substituted imidazo[4,5-b]pyridines are prepared and iterative, selective elaboration of functionalised imidazo[4,5-b]pyridin

Eco-friendly and facile synthesis of 2-substituted-1H-imidazo[4,5-b]pyridine in aqueous medium by air oxidation

We report a new environmentally-benign, convenient, and facile methodology for the synthesis of 2-substituted-1H-imidazo[4,5-b]pyridine. The reaction of 2,3-diaminopyridine with substituted aryl aldehydes in water under thermal conditions without the use

Hit generation and exploration: Imidazo[4,5-b]pyridine derivatives as inhibitors of Aurora kinases

A hit generation and exploration approach led to the discovery of 31 (2-(4-(6-chloro-2-(4-(dimethylamino)phenyl)-3H-imidazo[4,5-b]pyridin-7-yl)piperazin-1-yl)-N-(thiazol-2-yl)acetamide), a potent, novel inhibitor of Aurora-A, Aurora-B and Aurora-C kinases

A versatile method for the synthesis of benzimidazoles from o-nitroanilines and aldehydes in one step via a reductive cyclization

A highly efficient and versatile method for the synthesis of benzimidazoles was achieved in one step via the Na2S2O4 reduction of o-nitroanilines in the presence of aldehydes. Heating a solution of o-nitroaniline (Ic) and an aldehyde in EtOH or another appropriate solvent, in the presence of aqueous or solid Na2S2O4, provided facile access to a series of 2-substituted N-H benzimidazoles 5a-m containing a wide range of functional groups not always compatible with the existing synthetic methods. This methodology has also been applied to the regioselective synthesis of N-alkyl and N-aryl benzimidazoles 6a-f via the cyclization of the corresponding N-substituted nitroanilines 13a-e, respectively. In addition, the method was applied successfully to the synthesis of other imidazole containing heterocyclic ring systems such as 1H-imidazo[4,5-b]pyridines 14a,b and 1H-imidazo[4,5-f]quinoline 15.

Unambiguous structural assignment of monoanils obtained from 2,3-pyridinediamines

The reaction of 2,3-pyridinediamine la and its 5-bromo analogue lb independently with aromatic aldehydes results in the formation of 2-amino-and 5-bromo-2-amino-3-arylideneaminopyridines (2a and 2b) respectively. The structure of 2 has been confirmed by single crystal X-ray analysis, thereby ruling out the alternate structure for these compounds.

Structure and reactions of monoanils obtained from 2,3-pyridinediamines

The reaction of 2,3-pyridinediamines 1 with aromatic aldehydes results in the formation of 2-amino-3-arylideneaminopyridines 2 respectively. Dehydrogenative cyclisation of 2 with different reagents give 2-aryl-1H-imidazo[4,5-b]pyridines 4. Reactions of 2 with different reagents have been described.

Studies on aroylation of 2,3-pyridinediamines

The reaction of 2,3-pyridinediamine 1a and its 5-bromo analogue 1b, independently, with acid chloride or anhydride does not yield the diaroyl derivative and instead yields the cyclised product 3 or the monoaroyl derivative 4 depending upon the conditions.

Synthetic utility of catalytic Fe(III)/Fe(II) redox cycling towards fused heterocycles: A facile access to substituted benzimidazole, bis-benzimidazole and imidazopyridine derivatives

A catalytic Fe(III)/Fe(II) redox cycling approach has been examined and applied towards synthesis of a wide range of benzimidazole, bis-benzimidazole and imidazopyridine derivatives from oxidative coupling of aromatic ortho-diamines with aromatic as well

SITE SELECTIVE ALKOXYMETHYLATION OF IMIDAZOPYRIDINES: STRUCTURAL ANALYSIS BY HIGH FIELD NMR METHODS

The alkylation reaction of 2-aryl-1-(3)H-imidazopyridines (equivalent to 1-deazapurines) with alkoxymethyl chlorides and bromoacetonitrile are described.The structural assignments of the products were made by the use of two-dimensional 1H-1H NOE (NOESY) and selective INEPT (INAPT) 13C experiments utilizing polarization transfer from carbon-bound hydrogens in the alkyl side chains to selected 13C resonances via long range 3JCH couplings.Although three isomeric N-alkyl derivatives could arise from a single heterocycle based on considerations of tautomeric equillibria, however, the reactions exhibit marked site selectivity even under quite different reaction conditions.Thus, N-3 alkyl derivatives are produced exclusively in basic (Et3N/NaH) nonpolar media following an SE2cB mechanism.Solvent effects are evident in a loss of N-3 vs N-1 selectivity for alkylation when the polar aprotic solvent DMF is used.Under neutral conditions direct alkylation occurs at the N-4 position following an SE2' mechanism.The overall site selectivity appears to be governed by the relative reactivity of individual nucleophilic sites rather than the tautomeric composition in solution.

PREPARATION OF 2-ARYL-SUBSTITUTED IMIDAZOPYRIDINES AND IMIDAZOPYRIDINES

It is proposed that sulfur be used as the oxidizing agent in the synthesis of 2-arylimidazopyridines from o-diaminopyridines and aromatic (heteroaromatic) aldehydes.Benzyl alcohols and benzylpyridinium salts can be used in place of aldehydes. 2-Phenylimid