515129-89-2Relevant articles and documents
Electrophilic cyclization of aryldiacetylenes in the synthesis of functionalized enediynes fused to a heterocyclic core
Danilkina,Kulyashova,Khlebnikov,Br?se,Balova
, p. 9018 - 9045 (2015/01/08)
An efficient strategy for the synthesis of asymmetrically substituted enediynes fused to benzothiophene, benzofuran, and indole was developed. The proposed approach is based on the electrophilic cyclization of diacetylenes and Sonogashira coupling. Thus, iodocyclization of readily available ortho-functionalized (buta-1,3-diynyl)arenes was used as a direct way for the synthesis of 2-ethynyl-3-iodoheteroindenes. These substrates and their modified derivatives were easily converted by Sonogashira coupling with acetylenes to a variety of asymmetrically substituted acyclic enediynes fused to heterocycles. The tolerance of the developed methodology to a variety of functional groups is a great advantage in the synthesis of macrocyclic enediyne systems fused to a heterocyclic core. Synthesis of indole-fused 12-membered macrocyclic dienediyne was achieved using ring-closing metathesis as a key step.
Palladium-catalyzed cross-coupling reactions of 1,2-diiodoalkenes with terminal alkynes: Selective synthesis of unsymmetrical buta-1,3-diynes and 2-ethynylbenzofurans
Liang, Yun,Tao, Li-Ming,Zhang, Yue-Hua,Li, Jin-Heng
experimental part, p. 3988 - 3994 (2009/05/27)
(E)-1,2-Diiodoalkenes were found to be effective building blocks for the preparation of unsymmetrical buta-1,3-diynes and 2-ethynylbenzofurans. In the presence of palladium(II) acetate and copper(I) iodide, unsymmetrical buta-1,3-diynes were selectively o
A one-pot synthesis of 1-arylalka-1,3-diynes by sequential acetylene zipper and Sonogashira reactions
Balova, Irina A.,Morozkina, Svetlana N.,Knight, David W.,Vasilevsky, Sergei F.
, p. 107 - 109 (2007/10/03)
1,3-Diynes, formed in situ by base-induced acetylene zipper reactions, following anion quenching with water, undergo smooth Sonogashira-type couplings with functionalized aryl iodides, to give good overall yields of 1-arylalka-1,3-diynes.
