134478-87-8Relevant articles and documents
Iodonium-Induced Cyclization of N -Allenylindoles and N -Allenylpyrroles: An Access to Iododihydropyrido[1,2- a ]indoles and Dihydroindolizines
Grandclaudon, Charlotte,Michelet, Veronique,Toullec, Patrick Y.
, p. 310 - 313 (2018)
The formation of iodinated dihydropyrido[1,2- a ]indoles and dihydroindolizines was achieved by an iodocarbocyclization reaction of N -allenylindoles and N -allenylpyrroles. This transformation proceeded under very mild conditions using N -iodosuccinimide as the electrophilic iodine source to deliver the products via a 6- endo cyclization process. Careful choice of the solvent and concentration were mandatory to obtain the cyclization in good yields.
Tandem Carbenoid C-H Functionalization/Conia-ene Cyclization of N-Propargyl Indoles Generates Pyrroloindoles under Cooperative Rh(II)/Zn(II) Catalysis
Bhat, Aabid H.,Alavi, Sima,Grover, Huck K.
, p. 224 - 229 (2020)
The decomposition of diazodicarbonyl compounds in the presence of various metal catalysts has become a reliable method for the functionalization of indoles via carbenoid intermediates. Exploiting the nucleophilic reactivity of the in situ generated malonic ester product formed, we herein report a tandem C-H functionalization/Conia-ene cyclization of N-alkyne tethered indoles. This double functionalization of diazodicarbonyls generates a range of pyrrolo[1,2-a]-, pyrido[1,2-a]-, and azepino[1,2-a]indole products with good synthetic efficiency.
Harnessing the Polarizability of Conjugated Alkynes toward [2 + 2] Cycloaddition, Alkenylation, and Ring Expansion of Indoles
Pradhan, Tapas R.,Kim, Hong Won,Park, Jin Kyoon
supporting information, p. 5286 - 5290 (2018/09/12)
Reported is the utilization of electronically biased conjugated alkynes in the development of highly diastereo- and regioselective dearomative [2 + 2] cycloadditions, alkenylations, and ring expansions of electron-rich indoles. Regioselective protonations of cross- and linear-conjugated alkynes were found to be crucial for accessing various cyclobutene-fused indoline and alkenylated indole derivatives. Furthermore, the facile ring expansion of [2 + 2] keto adducts, which were successfully synthesized from ynones, provided 1H-benzo[b]azepine scaffolds.