61001-01-2

Usage

Structure

Imidazoisoquinoline core with a 4-methoxyphenyl group attached

Chemical Family

Isoquinoline

Potential Pharmaceutical Significance

Yes

Possible Applications

Medicinal chemistry, drug development targeting specific biological pathways or receptors

Current Research Status

Further research needed to understand potential uses and effects

Upstream product

• 1532-84-9 isoquinolin-1-ylamine 
• 2632-13-5 2-Bromo-4'-methoxyacetophenone 
• 39954-58-0 N-(p-Methoxyphenacyl)-isoquinoliniumbromide 
• 119-65-3 isoquinoline 
• 875289-81-9 2,4-dinitro-benzenesulfonic acid 2-(4-methoxy-phenyl)-2-oxo-ethyl ester 
• 93435-57-5 α-tosyloxy-p-methoxyacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 60-29-7 diethyl ether 
• 38435-51-7 4-methoxybenzenehydroximic acid chloride 
• 70-11-1 α-bromoacetophenone 
• 96155-57-6 1-(4-methoxyphenyl)ethanone O-acetyl oxime 

Downstream Products

• 86938-81-0 1-[2-(4-Methoxy-phenyl)-imidazo[2,1-a]isoquinolin-3-yl]-ethanone 
• 61001-18-1 2-(4-methoxyphenyl)-5,6-dihydroimidazo[2,1-a]isoquinoline 

Relevant academic research and scientific papers

Molecular iodine enabled generation of iminyl radicals from oximes: A facile route to imidazo[1,2-a]pyridines and its regioselective C-3 sulfenylated products from simple pyridines

An iodine promoted simple and environment friendly protocol has been developed to access imidazo[1,2-a]pyridines from unfunctionalized pyridines and oxime esters. This straightforward method efficiently converts the substrates into corresponding products affording moderate to good yields with large functional group tolerance. Additionally extensive investigation revealed that regioselective domino C-3 methyl sulfenylated imidazo[1,2-a]pyridines were also accessible first time from pyridines and oxime esters in DMSO solvent. The reaction operates through metal-free generation of iminyl radicals from easily accessible oxime esters, to build up the second heterocyclic ring on pyridines.

Conversion of pyridine to imidazo[1,2-a]pyridines by copper-catalyzed aerobic dehydrogenative cyclization with oxime esters

A rapid and environmentally friendly conversion of pyridine to imidazo[1,2-a]pyridines has been developed via copper-catalyzed aerobic dehydrogenative cyclization with ketone oxime esters.

Facile three-component domino reactions for the synthesis of 2-arylimidazo[1,2-a]pyridines and 2-arylimidazo[2,1-a]isoquinolines

The three-component domino reactions of pyridine/isoquinoline, phenacyl bromide, and substituted (E)-N-hydroxyarylimidoyl chloride in the presence of triethylamine afforded a series of 2-arylimidazo[1,2-a]pyridines and 2-arylimidazo[2,1-a]isoquinolines. This one pot three-component transformation presumably proceeds via ylide generation/annulation/fragmentation/dehydration domino sequence of reactions.

Synthesis of imidazo[2,1-a]isoquinolines from α-tosyloxyketones and 1-aminoisoquinoline in ionic liquid solvent

The room temperature ionic liquid n-butylpyridinium tetrafluoroborate (BPyBF4) is used as a 'green' recyclable alternative to classical molecular solvents for the cyclocondensation of α-tosyloxyketones with 1-aminoisoquinoline to prepare imidazo[2,1-a]isoquinolines in good yields.

Regioselective synthesis of 2-arylimidazo[2,1-a] isoquinolines

Substituted phenacyl bromides react with isoquinoline to form the corresponding quaternary salts which, when heated in ammonium acetate and acetic acid in the presence of Cu(II)O, undergo regioselective cyclisation to give 2-arylimidazo[2,1-a]isoquinoline

Synthesis and pregnancy terminating activity of 2-arylimidazo[2,1-a]isoquinolines and isoindoles

A series of 2-arylimidazo[2,1-a]isoquinolines (1-21), some 5,6-dihydro derivatives (22-28) and 2-phenyl-5H-imidazo[2,1-a]isoindole (29) were synthesized and tested for the pregnancy terminating activity in hamsters and rats. An efficient preparation of 2-

Antireproductive imidazo[2,1-a]isoquinoline compounds

Novel tricyclic compounds containing two ring notrogen atoms and represented by the following formula I STR1 wherein: A is one of the groups --CH2 --; --CH=CH--; and --CH2 --CH2 --; R is hydrogen, lower alkyl, lower alkoxy, lower alkenyloxy, lower alkynyloxy, cyclo(C3-6 alkyl)oxy, hydroxy, benzyloxy, halo, sulfamoyl, cyano, trifluoromethyl or nitro; R1 is hydrogen, lower alkoxy or halo; or R and R1 taken together are methylenedioxy; the sequence STR2 is one of the following moieties: STR3 WHEREIN R2 is hydrogen or lower alkyl; R3 is hydrogen or lower alkyl; R4 is hydrogen, methyl, carboxy, carbo(lower alkoxy), carbamyl, mono- or di-(lower alkyl) carbamyl or hydroxymethyl; provided that when the sequence STR4 is one of the moieties a) and b) wherein R2 is hydrogen or lower alkyl, A is not --CH=CH--; when the sequence STR5 is one of the moieties (a) and (b) wherein R2 is hydrogen, A is not --CH2 --; and when the sequence STR6 is one of the moieties (c) and (d) wherein R3 is hydrogen and when both R and R1 are hydrogen, A is not --CH=CH--; and the salts thereof with a non-toxic pharmaceutically-acceptable acid. The compounds of the invention have antireproductive activity.