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Nickel‐ or Palladium‐Catalyzed Stereoselective Synthesis of Tetrasubstituted Olefinic Indolines‐Fused Triazoles: Extension to the Spiroindoline Core
Author(s) -
Senadi Gopal Chandru,
Hu WanPing,
Boominathan Siva Senthil Kumar,
Wang JehJeng
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300760
Subject(s) - chemistry , stereoselectivity , palladium , alkyl , alkyne , catalysis , nickel , combinatorial chemistry , cascade , cascade reaction , fluorescence , organic chemistry , chromatography , physics , quantum mechanics
A nickel‐ or palladium‐catalyzed cascade approach to afford indolines‐fused triazoles with tetrasubstituted olefins in good yields with excellent control of regio‐ and stereoselectivity is described. We have also discussed the synthesis of unsaturated carbonyl species when the alkyne was appended to an alkyl chain. The synthetic methodology has been extended to construct the biologically active spiroindoline core via a vinylcylopropane (VCP) intermediate. The synthesized tetrasubstituted scaffolds were investigated for their photophysical properties and all of the them exhibited good absorption and fluorescence emission in the UV‐visible region.