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Tan JK, Mathiew M, Nayak S, et al. Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chem Asian J. 2017;12(13):1475-1479doi: 10.1002/asia.201700419.
Tan, J. K., Mathiew, M., Nayak, S., & Chan, P. W. H. (2017). Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chemistry, an Asian journal, 12(13), 1475-1479. https://doi.org/10.1002/asia.201700419
Tan, Javey Khiapeng, et al. "Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles." Chemistry, an Asian journal vol. 12,13 (2017): 1475-1479. doi: https://doi.org/10.1002/asia.201700419
Tan JK, Mathiew M, Nayak S, Chan PWH. Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chem Asian J. 2017 Jul 04;12(13):1475-1479. doi: 10.1002/asia.201700419. Epub 2017 Jun 13. PMID: 28608646.
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Chem Asian J. 2017 Jul 04;12(13):1475-1479. doi: 10.1002/asia.201700419. Epub 2017 Jun 13.

Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles.

Chemistry, an Asian journal

Javey Khiapeng Tan, Mitch Mathiew, Sanatan Nayak, Philip Wai Hong Chan

Affiliations

  1. School of Chemistry, Monash University, Clayton, Victoria, 3800, Australia.
  2. Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK.

PMID: 28608646 DOI: 10.1002/asia.201700419

Abstract

A synthetic method for the efficient assembly of benzo[c]carbazole derivatives that relies on silica gel-activated benzoic acid-mediated cycloaromatization of 1H-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/6π-electrocyclization pathway.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Brønsted acid; alkynes; homogeneous catalysis; nitrogen heterocycles; silica gel

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