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An Expeditious Benzannulation Reaction of Indol‐3‐yl‐but‐3‐yn‐2‐ols to Substituted 2‐Iodocarbazoles via Domino 5‐ endo Spirocyclization/Selective Vinyl Shift and Aromatization
Author(s) -
Yaragorla Srinivasarao,
Dada Ravikrishna,
Bag Debojyoti
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901393
Subject(s) - aromatization , chemistry , regioselectivity , cascade reaction , annulation , substrate (aquarium) , domino , combinatorial chemistry , ring (chemistry) , medicinal chemistry , catalysis , organic chemistry , oceanography , geology
Regioselective benzannulation reaction of indol‐3‐yl‐but‐3‐yn‐2‐ols to functionaly embellished 2‐iodocarbazoles is described for the first time using iodine at room temperature in an open flask. This reaction proceeds through a cascade of 5‐ endo spirocyclization, ring‐rearrangement through a vinyl shift, and aromatization in a short time. This protocol offers direct access to uncovered 2‐iodocarbazoles, with a broad substrate scope and good to moderate yields. Further, we have demonstrated the synthetic potential of these compounds using cross‐coupling reactions.