1429327-33-2Relevant academic research and scientific papers
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.
An acetylene zipper - Sonogashira reaction sequence for the efficient synthesis of conjugated arylalkadiynols
Kulyashova, Alexandra E.,Sorokoumov, Viktor N.,Popik, Vladimir V.,Balova, Irina A.
, p. 2235 - 2238 (2013/05/21)
We describe a new approach to the preparation of unsymmetrical arylalkadiynols, which is based on the isomerization of readily available internal alkadiynols into their terminal isomers followed by Sonogashira cross-coupling. The influence of the reaction conditions on the efficiency of the 'acetylene zipper' of alkadiynols is investigated. Unstable terminal diynols are used without isolation in Pd/Cu-catalyzed cross-couplings with iodoarenes bearing either electron-withdrawing or electron-donating substituents.
