103148-91-0Relevant academic research and scientific papers
One-pot synthesis of indolo[2,3-c]quinolin-6-ones by sequential photocyclizations of 3-(2-azidophenyl)-N-phenylacrylamides
Li, Zhanshan,Wang, Weixia,Zhang, Xiaotian,Hu, Congcong,Zhang, Wei
supporting information, p. 73 - 78 (2013/04/24)
A one-pot synthesis of indolo[2,3-c]quinolin-6(7H)-ones was achieved by sequential photocyclizations of 3-(2-azidophenyl)-N-phenylacrylamides in moderate to high yields. The reactions proceeded via photochemical cyclization of aryl azides to form N-phenylindol-2-carbamides and subsequent 6π-electrocyclic reaction and oxidative aromatization to afford the corresponding indolo[2,3-c]quinolin-6(7H)-ones. Georg Thieme Verlag Stuttgart · New York.
Cycloadditions, 9: Intramolecular Diels-Alder Reaction of Allenecarboxanilides; Incorporation of the Amide Nitrogen Atom in Benzo- and Dibenzo-condensated Five-, Six-, and Seven-membered Rings
Diehl, Klaus,Himbert, Gerhard
, p. 2874 - 2888 (2007/10/02)
The allenecarboxanilides 6a-f, the amide nitrogen atom of which is part of a benzo-condensated five-, six-, or seven-membered ring, are synthesized via phosphorus ylides.Thermolysis of 6 in refluxing xylene induces the intramolecular Diels-Alder reaction only in those cases, where the heterocycle is six- or seven-membered.The allenecarboxamide 6b with the six-membered ring bearing only one benzene nucleus in addition furnishes the quinoline derivatives 9 and 10 as main products, while in the case of the allenecarboxamides 6a,c possessing a five-membered heterocycle no reaction takes place whatever.It is tried to explain this different thermolytic behaviour by taking into consideration the spatial arrangement of the two reacting ?-systems (allene and arene) determined by the structure.
