848642-00-2Relevant academic research and scientific papers
Effect of water molecules on the cycloaromatization of non-conjugated aromatic tetraynes
Kawano, Tomikazu,Inai, Hiroki,Miyawaki, Kazuhiro,Ueda, Ikuo
, p. 944 - 949 (2007/10/03)
Cycloaromatization of the thienyl tetrayne 1, which was prepared in several steps from bis(trimethylsilyl)butadiyne and 3-bromothiophene-2-carbaldehyde, in benzene (0.33 mM) in the presence of molecular sieves 3A at room temperature gave the indeno[2,1-b]thiophene ring-fused 1H-2-benzopyran derivative 10 and indeno[2,1-b]thiophene derivative 11 in 11 and 40% yields, respectively. In contrast, cycloaromatization of 1 in the presence of water molecules at room temperature gave the indeno[2,1-b]thiophene ring-fused 1H-2-benzopyran derivative 10 and the indene ring-fused indeno[2,1-b]thiophene derivative 12 in 82 and 14% yields, respectively. Cycloaromatization of the phenyl tetrayne 9 in the presence of water molecules at room temperature also resulted in a dramatic change in product yields.
Synthesis of indenothiophenone derivatives by cycloaromatization of non-conjugated thienyl tetraynes
Kawano, Tomikazu,Inai, Hiroki,Miyawaki, Kazuhiro,Ueda, Ikuo
, p. 1233 - 1236 (2007/10/03)
Non-conjugated thienyl tetrayne derivatives 1-3 are prepared as novel building block for the construction of indenothiophenone derivatives. Oxidation of 1-3, followed by cycloaromatization of the corresponding ketone derivatives 13-15 proceeds smoothly to afford indenothiophenone derivatives 16-21 in good yields.
