Palladium/Copper Cocatalyzed C–H Activation and C–C Bond Regioselective Cleavage Reaction for the Synthesis of Fused Chromeno Quinolines

Abstract

A method for the synthesis of fused chromeno quinolines by the palladium/copper cocatalyzed C–H bond activation and C–C bond cleavage reaction has been developed. A variety of fused chromeno quinoline derivatives could be synthesized by coumarin derivatives and anilines through the C–C bond cleavage/C–H functionalization/C–C bond formation process. The MTT assay was used to evaluate the chromeno quinolines against the human cervix tumor cells (HeLa), 3c and 9c without coordination metals showed good inhibition effect.

La(OTf)3-Catalyzed [3+2] Cycloaddition Reactions for the Synthesis of Benzo[d]oxazoles/Benzofurans

“…The directly used reagents and solvents were of pure analytical grade and purchased from commercial sources, if not stated otherwise. The starting substrates were synthesized according to the known literature . Column chromatography was hand packed with silica gel (200–300 mesh).…”

“…At the same time, vinyl azides are a kind of important compound and can also be used as a substrate for cyclization reaction by rare earth . In continuation of our ongoing efforts to assemble heterocycles, here we reported the efficient La­(OTf) 3 -catalyzed [3+2] cycloaddition reactions for the synthesis of benzo­[ d ]­oxazoles/benzofurans via quinones and 1,2-di- tert -butyl-3-(cyanimino)­diaziridine (1,3-di- tert -butyl-2-cyanoguanidine)/vinyl azides.…”

Recent Advances in Green Synthesis of Functionalized Quinolines of Medicinal Impact (2018‐Present)

“…synthesized a series of Chromeno fused quinolines 69 (Scheme 18). [58] The reaction proceeded by C−H bond activation and C−C bond cleavage by Pd/Cu‐cocatalysis between substituted coumarin 67 and aromatic amines 68 . Activity of quinoline molecules was investigated against the human cervix tumor cells (HeLa).…”

“…[57] Firstly, N-sulfonylketenimine intermediate (formed by terminal alkynes 62 and sulfonylazides 63) reacted with aromatic amines 64 resulted in the formation of Nsulfonylamidines, which on reaction with isocyanides formed ). [58] The reaction proceeded by CÀ H bond activation and CÀ C bond cleavage by Pd/Cu-cocatalysis between substituted coumarin 67 and aromatic amines 68.…”

Novel UiO-NH2-like Zr-Based MOF (Basu-DPU) as an Excellent Catalyst for Preparation of New 6H-Chromeno[4,3-b]quinolin-6-ones

“…19−21 Chromeno quinolines display remarkable properties in biological, medicinal, and fluorescence areas (Figure 1). 22 Despite the significant role of fused chromeno quinolines in modern chemistry, efficient synthetic methods for their synthesis have rarely been presented. In general, the reported synthetic strategies for the synthesis of 6H-chromeno [4,3b]quinolin-6-ones used the Vilsmeier reagent or formyl group of aromatic aldehydes as the source of the methine (CH) group in the quinoline ring.…”