1228680-89-4

Upstream product

• 335159-82-5 3-(m-bromophenyl)propionyl chloride 
• 42287-90-1 3-(3-bromophenyl)propanoic acid 
• 52739-46-5 E-3-bromo-benzaldehyde-oxime 
• 497-19-8 sodium carbonate 

Downstream Products

• 67805-68-9 8-bromo-3,4-dihydroquinolin-2(1H)-one 
• 3279-90-1 6-bromo-3,4-dihydro-1H-quinolin-2-one 

Relevant academic research and scientific papers

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

Revisiting Arene C(sp2)?H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C?H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.

SUBSTITUTED PHENYLACETYLENES, PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS AND PROCESSES FOR THE PREPARATION OF THESE COMPOUNDS AND COMPOSITIONS

Substituted phenylacetylenes of the formula STR1 wherein one of the groups R1 is a hydrogen atom and the other represents the group of the formula STR2 in which R3 is hydrogen, methyl or ethyl and R4 is a methyl or an amino group and wherein R2 represents mono- or binuclear aromatic or heterocyclic residues containing sulfur, nitrogen or oxygen as hetero atoms and optionally being substituted by 1 to 3 substituents as defined, which specifically inhibit 5-lipoxygenase and are useful in pharmaceutical compositions for prophylaxis and treatment of diseases due to the action of leukotrienes. The compounds may be prepared by reacting a compound of the formula STR3 wherein R2 has the same meaning as above and one of the groups R7 is a hydrogen atom and the other represents the group of the formula --COR3, with hydroxylamine to form the oxime which then is reduced to the corresponding hydroxylamine compound into which the group of the formula --COR4 is introduced.