22408-61-3

Upstream product

• 143-33-9 sodium cyanide 
• 38464-20-9 4-chloro-3-nitro-chromen-2-one 
• 10523-48-5 3-cyano-4-hydroxycoumarin 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 50329-91-4 4-chloro-3-formylcoumarin 
• 858918-91-9 C₁₀H₆ClNO₃ 

Downstream Products

• 871131-52-1 4-amino-5H-[1]benzopyrano[4,3-d]pyrimidin-5-one 

Relevant academic research and scientific papers

Synthesis and structure of novel 3,4-annelated coumarin derivatives

(Chemical Equation Presented) Condensation of 4-chloro-2-oxo-2H-chromene-3- carbonitrile (1) with heteroarylamines 2a-d in acetonitrile containing a catalytic amount of triethylamine followed by spontaneous intramolecular cyclization gave the novel coumarin derivatives 3a-d, respectively. These compounds underwent acid hydrolysis giving the corresponding oxoderivatives 4a-d. The structural assignments of the synthesized compounds were based on elemental, IR, 1H and 13C NMR analyses.

Synthesis of 6H,7H-chromeno[3′,4′:4,5]thieno[3,2-b]indol-6-ones using the Fischer indolization reaction

A series of 6H,7H-chromeno[3′,4′:4,5]thieno[3,2-b]indol-6-ones, bearing thieno[3,2-b]indole and coumarin parts in their fused molecules, were readily prepared using one-pot procedure based on reaction of 3-aminothieno[3,2-c]coumarins, in situ formed from 3-aminothieno[3,2-c]coumarin-2-carboxylates, with arylhyrazines according to the Fischer indole synthesis. In turn, the synthesis of methyl 3-aminothieno[3,2-c]coumarin-2-carboxylates were carried out in two steps from available 4-hydroxycoumarins. To this end, 4-hydroxycoumarins were successively treated with POCl3-DMF complex and hydroxylamine hydrochloride to obtain 4-chloro-3-cyanocoumarins. The latter substrates further reacted with methyl thioglycolate in the presence of NaOMe to give the required 3-aminothiophene-2-carboxylate precursors.

An efficient route for synthesis and reactions of seleno[2, 3-c]coumarin

Synthesis of new selenium-containing coumarin moiety via the reaction of 4-chloro-2-oxo-2H-chromene-3-carbonitrile with selenium and sodium borohydride gave 3-cyano-4-coumarinselenol which reacted with different halo-acids, such as chloroacetonitrile, eth

Unexpected synthesis of three components from the reaction of 4-chloro-3-formylcoumarin with hydroxylamine hydrochloride

A mild and simple oximation reaction of 4-chloro-3-formylcoumarin with hydroxylamine hydrochloride in basic medium gave unexpected three components via oxime.Those compounds were separatedin good yields by preparative TLC and by chemical means using diffe

Synthesis and antimicrobial activity of new heterocyclic compounds containing thieno[3,2-c]coumarin and pyrazolo[4,3-c]coumarin frameworks

Reaction of 4-chlorocoumarin-3-carbonitrile with ethyl thioglycolate and ethyl glycinate hydrochloride leads to a series of title products. Hydrazinolysis of amino thienocoumarin carboxylate afforded the hydrazino derivative which underwent various reactions to build new heterocyclic rings containing thienocoumarin moiety. Chloro acetylation of aminoester compound afforded the chloro acetyl amino which underwent nucleophilic substitution reactions with various amines. The following treatment with formaldehyde under Mannich conditions afforded the corresponding imidazo derivatives. Reaction of chloroacetylamino with potassium thiocyanate yielded ethylpyrimidothieno coumarin sulfanylacetate which was used as a versatile precursor for synthesis of other heterocycles. On the other hand, reaction of chloro coumarin carbonitrile with hydrazine gave the aminopyrazolocoumaine which reacted with bifunctionally compounds to give the substituted pyrimido derivatives. Diazotization and coupling of aminopyrazole with ethylcyanoacetate yielded ethylaminotriazinopyrazolocoumarine carboxylate. Several of the compounds obtained demonstrated considerable antifungal and antibacterial activity in the in vitro test systems.