1384480-00-5Relevant articles and documents
Reactions of HDDA-Derived Benzynes with Perylenes: Rapid Construction of Polycyclic Aromatic Compounds
Xu, Feng,Xiao, Xiao,Hoye, Thomas R.
, p. 5636 - 5639 (2016)
Benzynes produced by the thermal cycloisomerization of tetrayne substrates [i.e., by the hexadehydro-Diels-Alder (HDDA) reaction] react with perylenes to produce novel naphthoperylene derivatives. Cyclic voltammetry and absorption and emission properties of these compounds are described. DFT studies shed additional light on the dearomatization that accompanies the reaction as well as some of the spectroscopic behavior.
Epoxyanthracene Derivatives and Dicarbonylation on Benzene Ring via Hexadehydro-Diels-Alder (HDDA) Derived Benzynes with Oxazoles
Yang, Feihu,Zheng, Xiaojie,Lei, Yu,Hu, Qiong,Zhu, Wenjing,Hu, Yimin
, p. 1125 - 1133 (2021/11/22)
A capture reaction of hexadehydro-Diels-Alder (HDDA) derived benzyne with various substituted oxazoles is reported. With methyl, hydrogen, or phenyl as the substituent at 2-position of oxazole, tetraynes afforded epoxyanthracene derivatives or underwent dicarbonylation on benzene ring. The reaction does not require any catalyst or additive. The mechanism behind the reaction was investigated. The obtained polycyclic product structure has potential application value in optoelectronic materials. The availability of dicarbonylated arene implies the uniqueness of HDDA benzyne reaction compared with traditional benzyne.
Silver-Catalyzed Annulation of Arynes with Nitriles for Synthesis of Structurally Diverse Quinazolines
Ghorai, Sourav,Lin, Yongjia,Xia, Yuanzhi,Wink, Donald J.,Lee, Daesung
, p. 626 - 630 (2020/01/31)
An efficient silver catalyzed annulation reaction of aryne with nitriles to generate quinazolines is described. Arynes generated from triynes or tetraynes through a hexadehydro Diels-Alder reaction readily participated in an [A + 2B] mode of annulation with nitriles in the presence of AgSbF6 catalyst. The mechanism was explored by DFT calculations, which supports the silver-catalyzed formation of nitrilium ion as a key intermediate. This annulation generates an array of polysubstituted novel quinazoline derivatives with excellent regioselectivity.
Phenanthrenes/dihydrophenanthrenes: The selectivity controlled by different benzynes and allenes
Yao, Liangliang,Fang, Bo,Hu, Qiong,Lei, Yu,Bao, Li,Hu, Yimin
, p. 15185 - 15188 (2020/12/21)
A method for the intermolecular annulation of benzynes with allenes is disclosed. This protocol utilized allenes as an unconventional diene component for the selective synthesis of phenanthrenes and dihydrophenanthrenes under the control of different benzyne precursors, featuring high atom-economy and good functional group compatibility. Density functional theory (DFT) calculations reveal that different migratory routes of the aromatic C-H bond are crucial for the observed selectivity. This journal is