Rhodium Catalyzed [2π + 2π + 2π]-Cycloaddition of Alkynyl-Ynamides and Carbon Disulfide to Indolo-Thiopyrane Thiones  

作　　者：Benjamin Dassonneville Felix Hinkel Heiner Detert Benjamin Dassonneville;Felix Hinkel;Heiner Detert(Department of Chemistry, Johannes Gutenberg University Mainz, Mainz, Germany)

机构地区：[1]Department of Chemistry, Johannes Gutenberg University Mainz, Mainz, Germany

出　　处：《International Journal of Organic Chemistry》2023年第1期16-39,共24页有机化学国际期刊（英文）

摘　　要：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.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.

关 键 词：CYCLOADDITION Heterocycles Rhodium Sulfur ALKYNE 

分 类 号：O62[理学—有机化学]