53995-92-9

Upstream product

• 71-43-2 benzene 
• 606-43-9 1-methyl-2-quinolin-2(1H)-one 
• 100-52-7 benzaldehyde 
• 67984-94-5 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 

Relevant academic research and scientific papers

Metal-Free, Regioselective, Dehydrogenative Cross-Coupling between Formamides/Aldehydes and Coumarins by C–H Functionalization

A highly efficient, single-step, metal-free synthetic approach to the synthesis of coumarin-3-carboxamides has been developed. The protocol employs tert-butyl peroxybenzoate as a radical initiator to achieve the regioselective carboxamidation of coumarins at C-3 in good-to-moderate yields. The established reaction protocol offers a wide substrate scope as it allows the use of both formamides as well as aldehydes as coupling partners with excellent regioselectivity. Furthermore, mechanistic investigations illustrate that the reaction proceeds by a free-radical pathway.

Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position acting as dienophiles with dienes

Diels-Alder cycloadditions of 2(1H)-quinolones having an electron-withdrawing group at the 3-position with alkyl- and silyloxy-1,3-butadienes (2a, b) were carried out to give phenanthridones richly functionalized regio- or stereoselectively under conditions of atmospheric and high pressure. Furthermore, regioselectivity and chemoselectivity of 3-substituted 2 (1H)-quinolones to 2a, b were examined using MO calculation.