148149-21-7

Upstream product

• 50458-78-1 ethyl isoquinoline-1-carboxylate 
• 100-46-9 benzylamine 
• 486-73-7 1-isoquinolinecarboxylic acid 
• 119-65-3 isoquinoline 
• 88333-03-3 Benzyl isocyanide 
• 22003-17-4 O-phenyl N-benzylcarbamate 
• 16956-42-6 N-(phenylmethyl) hydrazine carboxamide 

Downstream Products

• 19382-37-7 3-phenylimidazo<5,1-a>isoquinoline 

Relevant academic research and scientific papers

Direct C-H aminocarbonylation ofN-heteroarenes with isocyanides under transition metal-free conditions

A C-C bond forming amide synthesis through direct C-H aminocarbonylation ofN-heteroarenes with isocyanides was developed. The reaction was mediated by an inorganic persulfate salt under transition metal-free conditions. Mechanistic studies suggested a radical pathway for this reaction without the participation of H2O and O2. This method also showed merits of substrate availability, easy operation and atom economy. It provided an efficient route for straightforward synthesis ofN-heteroaryl amides.

Highly Regioselective Carbamoylation of Electron-Deficient Nitrogen Heteroarenes with Hydrazinecarboxamides

The use of hydrazinecarboxamides as a new class of carbamoylating agents has been established through the dehydrazinative Minisci reaction of electron-deficient nitrogen heteroarenes. A wide range of electron-deficient nitrogen heteroarenes, including isoquinoline, quinoline, pyridine, phenanthridine, quinoxaline, and phthalazine, underwent copper/acid-catalyzed oxidative carbamoylation with hydrazinecarboxamide hydrochlorides to afford structurally diverse nitrogen-heteroaryl carboxamides as single regioisomers in moderate to excellent yields. The functional group tolerance was substantially demonstrated in the direct carbamoylation of quinine obviating multistep sequences involving protecting groups and prefunctionalization of the heterocycle.

Synthesis and research of benzylamides of some isocyclic and heterocyclic acids as potential anticonvulsants

A series of benzylamides of isocyclic and heterocyclic acids was synthesized and tested in Anticonvulsant Screening Project (ASP) of Antiepileptic Drug Development Program (ADDP) of NIH. Near all synthesized derivatives of heterocyclic acids showed activity. All obtained derivatives of mono- and bicyclic isocyclic acids were inactive. The power of action of heterocyclic acids derivatives seems does not depend upon kind of heteroatom (N, O or S). One of the compounds (2-furoic acid benzylamide (4)) appeared most promising. It showed in minimal clonic seizure (6Hz) test (ASP) in rats after i. p. administration: MES ED50 = 36.5 mg/kg, TOX TD50 = 269.75 mg/kg, and PI = 7.39.

Aryl triflates and [11C]/(13C)carbon monoxide in the synthesis of 11C-/13C-amides

Palladium(0)-mediated carbonylation reactions using aryl triflates, amines, and a low concentration of [11C]carbon monoxide were used in the syntheses of 13 11C-labeled amides. Lithium bromide was used as an additive to facilitate the reaction. The 11C-labeled products were obtained with decay-corrected radiochemical yields in the range of 2-63%. The radiochemical purity of the final products exceeded 98%. As an example, a reaction starting with 1.79 GBq [11C]carbon monoxide gave 0.38 GBq of LC-purified N-isopropyl-4-nitro-[11C]benzamide within 27 min from the start of the carbonylation reaction (54% decay-corrected radiochemical yield). The specific radioactivity of this compound was 191 GBq/μmol, 35 min after the end of a 10 μAh bombardment. N-Benzyliso-quinoline-1-(13C)carboxamide was prepared and analyzed by NMR for confirmation of the labeling position. The triflates 16, 20, 21, and 22 were synthesized from the corresponding alcohols and trifluoromethanesulfonic anhydride. The reference compounds 30a and 30b were prepared from the corresponding carboxylic acids and benzylamine. The other nine reference compounds 32a to 32i were synthesized from the respective acid chlorides and amines. The presented report shows that the sometimes more easily obtainable aryl triflates can be a useful alternative to the commonly used aryl halides in palladium(0)-mediated synthesis of 11C/13C-amides.

Studies on Wallach's Imidazole Synthesis

The reaction of the N-benzylamides of N-heterocyclic carboxylic acids 3 and 6-9 with phosphorus pentachloride affords heterocondensed imidazoles 4 and 10-14 by a scheme reminiscent of Wallach's imidazole synthesis starting from N,N'-dialkyloxamides.Kinetic and labelling experiments are described which support a mechanism involving nitrile ylide species and allow a better understanding of the Wallach reaction.The limiting parameter for the formation of heteroanellated imidazoles is the electron availability of the heterocyclic ring.