74123-81-2

Upstream product

• 36198-21-7 1-(4-bromo-1,3-dimethyl-1H-pyrazol-5-yl)-3-phenylurea 
• 98-80-6 phenylboronic acid 
• 3524-32-1 5-Amino-1,3-dimethylpyrazole 
• 103-71-9 phenyl isocyanate 

Relevant academic research and scientific papers

The Suzuki-Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction

The efficient Suzuki-Miyaura cross-coupling reaction of halogenated aminopyrazoles and their amides or ureas with a range of aryl, heteroaryl, and styryl boronic acids or esters has been developed. The method allowed incorporation of problematic substrates: aminopyrazoles bearing protected or unprotected pyrazole NH, as well as the free amino or N-amide group. Direct comparison of the chloro, bromo, and iodopyrazoles in the Suzuki-Miyaura reaction revealed that Br and Cl derivatives were superior to iodopyrazoles, as a result of reduced propensity to dehalogenation. Moreover, the mechanism and factors affecting the undesired dehalogenation side reaction were revealed.

Fused isoquinoline derivatives

Fused isoquinoline derivatives of the general formula STR1 wherein: A is a divalent radical selected from the groups STR2 wherein R3 and R4 each independently represents hydrogen, alkyl,, alkenyl, cycloalkyl, aryl, aralkyl, aralkenyl, cycloalkyl-alkyl or, taken together with the adjacent double bond, represent a cycloalkene containing from 5 to 8 carbon atoms or an aromatic nucleus; R5 represents hydrogen, hydroxyl, alkyl, alkenyl, cycloalkyl, aryl, aralkyl, aralkenyl or cycloalkyl-alkyl; Y is =O, =S or =NH; X is --O--, --S-- or --NR6 -- wherein R6 represents hydrogen, alkyl, cycloalkyl, aryl, aralkyl or cycloalkyl-alkyl; R1 and R2 each independently represents hydrogen, alkyl, phenyl, cycloalkyl, alkoxy, alkenyloxy, methylenedioxy, cycloalkoxy, halo or di-alkylamino or, taken together with the adjacent carbon atoms of the benzene ring, form a cycloalkenyl group containing 5 or 6 carbon atoms or an aromatic nucleus fused on the benzene ring. The compounds are essentially prepared through thermal cyclization of a compound of the formula STR3 wherein A, X, Y, R1 and R2 have the same meanings given before, with the proviso that R1 and R2 cannot simultaneously occupy both the ortho positions, B represents hydrogen, R represents an --OR7 or --NR8 R9 radical wherein R7 is alkyl, aryl or aralkyl and R8 and R9 each independently represents hydrogen, alkyl, aryl, aralkyl, or taken together with the adjacent nitrogen atom represent a heterocyclic saturated radical of 5 or 6 atoms which may contain a further hetero-atom selected from oxygen and nitrogen, or the symbols B and R taken together represent a further bond between the adjacent carbon and nitrogen atoms.