Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration | Zendy

Srinivasarao Yaragorla | Zendy; Debojyoti Bag | Zendy; Ravikrishna Dada | Zendy; K. V. Jovan Jose | Zendy

Open Access

Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration

Author(s) -

Srinivasarao Yaragorla,

Debojyoti Bag,

Ravikrishna Dada,

K. V. Jovan Jose

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.8b02393

Subject(s) - cycloisomerization , alkyl , chemistry , aryl , atom economy , substrate (aquarium) , propargyl , combinatorial chemistry , solvent , organic chemistry , medicinal chemistry , catalysis , biology , ecology

Herein, we disclose the first report on iodo-cycloisomerization of 1-(indol-3-yl)-1-arylbut-3-yn-2-ols to form 3-iodocarbazoles. The synthesis proceeds through a cascade 5-endo-spirocyclization, followed by selective 1,2-alkyl migration. This method governs the green synthesis principles such as open-flask reaction, AcOEt as the solvent, rt reaction with short time, use of iodine, and broad substrate scope with atom and step economy.

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