One-pot Fischer indolisation indole N-alkylation enables straightforward, rapid synthesis of structurally-diverse 1,2,3-trisubstituted indoles from simple, widely-available precursors.

A range of brominated indole derivatives were found in the egg masses of six species of muricid molluscs. Several non-brominated indoles were also present in the eggs of two Mediterranean Muricidae, although these were not found in the Australian species. Tyrindoleninone (3), was the only compound found in all six species and is likely to be responsible for the observed antimicrobial activity o...

2,3-Fused indoles are found in numerous natural products and drug molecules. Although several elegant methods for the synthesis of this structural motif have been reported, long reaction times and harsh conditions are sometimes required, and the yields tend to be low. Herein, we report a microwave method for straightforward access to various types of 2,3-fused indoles via AgSbF6-catalysed intra...

Amild and selective C–H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH)...

The direct C-H annulation of anilines or related compounds with internal alkynes provides straightforward access to 2,3-disubstituted indole products. However, this transformation proceeds with poor regioselectivity in the synthesis of unsymmetrically 2,3-diaryl substituted indoles. Herein, we report the rhodium(III)-catalyzed C-H annulation of nitrones with symmetrical diaryl alkynes as an alt...

This paper describes azidation of indoles with NaN3 and ceric ammonium nitrate (CAN), giving a variety of spirocyclic 2-azido indolines in good yields and moderate diastereoselectivities.

Silver(I) triflate efficiently catalyzes the tandem reaction of acetylenic aldehydes with indoles to give highly substituted tetrahydrocarbazoles in high yields.

Vilsmeier-Haack reaction of 2,3,3-trimethyl-3H-benzo[g]indole, then aqueous basic work-up, leads to benzo[g]indol-2-ylidene- malondialdehydes. These react with various arylhydrazines and quinolin-2-ylhydrazine to form 3,3-dimethyl-2-(1-aryl-1H-pyrazol-4-yl)- 3H-benzo[g]indoles in good yields.

We described two orthogonal heterocycle syntheses, where an arene bearing both an alkyne and a triazene functionality underwent two distinct cyclization pathways mediated by different transition metals. Starting from the same substrates, a synthesis of 2H-indazole was accomplished by a Cu(II) salt promoted oxidative cyclization, while 2-substituted indoles could be accessed via a Ag(I) salt med...