724-15-2

Upstream product

• 13109-11-0 4-chloro-3-phenylcinnoline 
• 13141-38-3 2-phenylethynylaniline 
• 536-74-3 phenylacetylene 
• 1207666-88-3 C₁₄H₉N₂⁽¹⁺⁾*HO₄S^(1-) 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 70-11-1 α-bromoacetophenone 
• 10604-22-5 3-phenylcinnoline 

Relevant academic research and scientific papers

Multicomponent Coupling Cyclization Access to Cinnolines via in Situ Generated Diazene with Arynes, and α-Bromo Ketones

A transition-metal-free multicomponent coupling cyclization reaction was explored involving arynes, tosylhydrazine, and α-bromo ketones. The reaction proceeds via a formal [2 + 2 + 2] cycloaddition, giving access to cinnoline derivatives in moderate yields under mild conditions. Three chemical bonds were formed-two C-N bonds and one C-C bond-in a single step.

The effect of substrate structure on the direction of cyclization of ortho-alkynylbenzene diazonium salts

The cyclization of ortho-(arylethynyl)benzene diazonium salts (the Richter reaction) is studied. A reaction mechanism, which differs radically from that reported earlier is proposed and substantiated by experimental data and quantum-chemical calculations.

Solid-phase synthesis of substituted cinnolines by a Richter type cleavage protocol

Starting from triazene bound ortho-halo arenes on a solid support, palladium-catalyzed alkynylations and subsequent cleavage reactions under acidic conditions give rise to ortho-alkynylaryldiazonium salts, which in turn undergo cyclization to afford substituted 4-halo- and 4- hydroxycinnolines in moderate to good yields. The method is applicable to automated synthesis.

Cinnolines and Pyrazolopyridazines. - Novel Synthetic and Mechanistic Aspects of the Richter Reaction

The thermal cyclization of 2-alkynylbenzenediazonium salts 2 known as the Richter reaction and leading, as described in the literature, only to 4-hydroxycinnolines 6 has been studied.A new probable route to these compounds involving intermediate formation