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