18514-84-6

Usage

Synthesis Reference(s)

Synthesis, p. 288, 1987 DOI: 10.1055/s-1987-27921

InChI:InChI=1/C8H6N2O/c11-8-5-9-10-7-4-2-1-3-6(7)8/h1-5H,(H,10,11)

Upstream product

• 119-61-9 benzophenone 
• 18514-85-7 4-oxo-1,4-dihydrocinnoline-3-carboxylic acid 
• 408508-53-2 4-phenoxy-cinnoline 
• 64-17-5 ethanol 
• 16433-96-8 2-ethynyl-1-nitrobenzene 
• 551-93-9 2-aminoacetophenone 
• 109773-41-3 4-Oxo-3-triphenylphosphoranylidene-3,4-dihydrocinnoline 
• 111054-05-8 1-(2-Amino-phenyl)-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 111054-09-2 3-(2-Nitro-phenyl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid tert-butyl ester 
• 134-20-3 2-carbomethoxyaniline 
• 530-85-8 3-(2-nitrophenyl)-2-propynoic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 111054-12-7 1-(2-nitrophenyl)-2-(triphenylphosphoranylidene)ethanone 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 1556-22-5 1-methylcinnolin-4(1H)-one 
• 4964-44-7 2-methylcinnolin-2-ium-4-olate 
• 253-66-7 Cinnoline 
• 5152-84-1 4-chlorocinnoline 
• 93334-81-7 1-Acetyl-4-cinnolon 
• 170646-73-8 3-(4-Oxo-4H-cinnolin-1-yl)-propionic acid methyl ester 
• 82453-00-7 3-iodocinnoline 
• 82452-99-1 4-chloro-3-iodocinnoline 
• 82453-35-8 3-phenylethynylcinnoline 
• 82453-26-7 E-3-phenylethenyl-4(1H)cinnolinone 
• 82453-11-0 2-phenyl-1H-pyrrolo<3,2-c>cinnoline 
• 82453-10-9 2-phenylfuro<3,2-c>cinnoline 
• 335242-55-2 3-bromo-1H-cinnolin-4-one 
• 1126475-27-1 1-(3-carboxy-4-fluorobenzyl)-4-oxo-1,4-dihydrocinnolin-1-ium chloride 

Relevant academic research and scientific papers

NOVEL CANNABINOID RECEPTOR LIGANDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND PROCESS FOR THEIR PREPARATION

The present invention relates to compounds of f formula (I) as cannabinoid receptor modulators, in particular cannabinoid 1 (CB1) or cannabinoid 2 (CB2 ) receptor modulators, and uses thereof f or treating diseases, conditions and/or disorders modulated by a cannabinoid receptor ( such as pain, neurodegenrative disorders, eating disorders, weight loss or control, and obesity).

On the tautomerism of cinnolin-4-ol, cinnoline-4-thiol, and cinnolin-4-amine

Detailed NMR spectroscopic investigations (1H, 13C, 15N) with cinnolin-4-ol (1) reveal this compound to exist exclusively in the cinnolin-4(1H)-one form in deuteriodimethyl sulfoxide solution. This finding is confirmed by comparison of the NMR spectroscopic data of 1 with those of the corresponding 'fixed' O-methyl and N-methyl derivatives, i.e. 4-methoxycinnoline (3) and 1-methylcinnolin-4(1H)-one (5). Similarly, cinnoline-4-thiol (4) is present in the thione form in deuteriodimethyl sulfoxide, whereas cinnolin-4-amine (7) exists in the amino form. In addition, in-depth analyses of the NMR spectra of some simple 4-substituted cinnolines are provided.

A New Facile Synthesis of 4-Oxo-1,4-dihydrocinnolines

2-(2-Aminoaryl)-2-oxo-triphenylphosphoniumethylides 2a-d, readily available by standard procedures, are converted into 4-oxo-1,4-dihydrocinnolines 7a-d by treatment with nitrous acid and subsequent basic hydrolysis of the intermediate phosphoranes 6a-d.