New synthetic methods for 2,3-diarylacridin-9(10H)-one and (E)-2-aryl-4-styrylfuro[3,2-c]quinoline derivatives

作者：Silva Vera L M^*; Silva Artur M S

来源：Tetrahedron, 2014, 70(34): 5310-5320.

DOI：10.1016/j.tet.2014.05.040

• N-Methylation
• Heck reaction
• Electrocyclization reactions
• Acridin-9(10H)-ones
• Furoquinolines

Two new synthetic methodologies for 2,3-diarylacridin-9(10H)-ones were developed. The first one involves the Heck reaction of (E)-3-iodo-2-styrylquinolin-4(1H)-ones with styrenes, leading to (E,E)-2,3-distyrylquinolin-4(1H)-ones, which when heated at high temperatures cyclize in two different ways. Electrocyclization and further in situ oxidation leads to 2,3-diarylacridin-9(10H)-ones, while tautomerization, cyclization by nucleophilic addition and further in situ oxidation produces (E)-2-aryl-4-styrylfuro[3,2-c]quinolines as the main compound. The second method gives only 2,3-diaryl-10-methylacridin-9(10H)-ones and involves the Heck reaction of (E)-3-iodo-1-methyl-2-styrylquinolin-4(1H)-ones and styrenes, leading to (E,E)-1-methyl-2,3-distyrylquinolin-4(1H)-ones, which when heated at high temperatures cyclize through electrocyclization and oxidation processes affording the expected compounds. The structures of all new compounds were established by extensive NMR studies.

• 出版日期2014-8-26