Au-Catalyzed Synthesis of Thiopyrano[2,3-b]indoles Featuring Tandem Rearrangement and Hydroarylation

Mukund Jha; Shiv Dhiman; T Stanley Cameron; Dalip Kumar; Anil Kumar

doi:10.1021/acs.orglett.7b00617

Au-Catalyzed Synthesis of Thiopyrano[2,3-b]indoles Featuring Tandem Rearrangement and Hydroarylation

Org Lett. 2017 Apr 21;19(8):2038-2041. doi: 10.1021/acs.orglett.7b00617. Epub 2017 Apr 5.

Authors

Mukund Jha¹, Shiv Dhiman^{1

2}, T Stanley Cameron³, Dalip Kumar², Anil Kumar²

Affiliations

¹ Department of Biology and Chemistry, Nipissing University , North Bay, ON P1B 8L7, Canada.
² Department of Chemistry, Birla Institute of Technology and Science , Pilani, Pilani 333031, India.
³ Department of Chemistry, Dalhousie University , Halifax, NS B3H 4J3, Canada.

PMID: 28378595
DOI: 10.1021/acs.orglett.7b00617

Abstract

Gold(III)-catalyzed synthesis of 14-π electron heteroaromatic thiopyrano[2,3-b]indole is reported using conjugated enyne tethered indole sulfides, featuring skeletal rearrangement conjoined with intramolecular hydroarylation (via C3-H functionalization of the indole core) and oxidative aromatization. Subsequent Pd-catalyzed C-C coupling resulted in a 16-π electron heteroaromatic isothiochromeno[1,8,7-bcd]indole.

Publication types

Research Support, Non-U.S. Gov't