Author(s)

Benjamin Dassonneville, Felix Hinkel, Heiner Detert^*

Department of Chemistry, Johannes Gutenberg University Mainz, Mainz, Germany.

The synthesis of new indoloannulated thiopyranethiones is reported. The key-step is a rhodium-catalyzed [2 + 2 + 2]-cycloaddition of alkynyl-ynamides with carbon disulfide to close the pyrrole and the thiopyranethione rings simultaneously. A violet idolothiopyrane thione or a mixture of the violet and a red isomer result from [RhCl(C₈H₁₄)₂]₂/3BINAP catalyzed cycloadditions, the regiochemistry is controlled by the substitution pattern on the alkynyl-ynamide.

Cycloaddition, Heterocycles, Rhodium, Sulfur, Alkyne

Dassonneville, B. , Hinkel, F. and Detert, H. (2023) Rhodium Catalyzed [2π + 2π + 2π]-Cycloaddition of Alkynyl-Ynamides and Carbon Disulfide to Indolo-Thiopyrane Thiones. International Journal of Organic Chemistry, 13, 16-39. doi: 10.4236/ijoc.2023.131003.