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Brønsted Acid‐Mediated Cycloaromatization of 1 H ‐Indol‐2‐yl Propargyl Benzoates to 7 H ‐Benzo[ c ]carbazoles
Author(s) -
Tan Javey Khiapeng,
Mathiew Mitch,
Nayak Sanatan,
Chan Philip Wai Hong
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700419
Subject(s) - benzoates , chemistry , benzoic acid , stereochemistry , brønsted–lowry acid–base theory , organic chemistry , catalysis
A synthetic method for the efficient assembly of benzo[ c ]carbazole derivatives that relies on silica gel‐activated benzoic acid‐mediated cycloaromatization of 1 H ‐indol‐2‐yl propargyl benzoates under atmospheric conditions is described. Robust with a variety of substitution patterns tolerated, the reaction provides a one‐step strategy to construct a member of the N ‐heterocycles family in good to excellent yields. A tentative mechanism is proposed in which the cycloaromatization process is thought to involve a Brønsted acid‐mediated formal 1,3‐acyloxy migration/6 π ‐electrocyclization pathway.