Brønsted Acid‐Mediated Cycloaromatization of 1 H ‐Indol‐2‐yl Propargyl Benzoates to 7 H ‐Benzo[ c ]carbazoles | Zendy

Tan Javey Khiapeng | Zendy; Mathiew Mitch | Zendy; Nayak Sanatan | Zendy; Chan Philip Wai Hong | Zendy

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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.

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