Multi-catalysis reactions: direct organocatalytic sequential one-pot synthesis of highly functionalized cyclopenta[b]chromen-1-ones

Abstract

We have developed a new technology called multi-catalysis for the sequential one-pot synthesis of highly functionalized heterocycles. A practical and novel multi-component aniline-, self- and Brønsted acid-catalyzed selective process for the sequential one-pot synthesis of highly substituted 2-(2-hydroxy-aryl)-cyclopentane-1,3-diones, 3,9-dihydro-2H-cyclopenta[b]chromen-1-ones and 3,3-dimethyl-2,3,4,9-tetrahydro-xanthen-1-ones is reported. Direct combination of aniline- and self-catalyzed cascade olefination–hydrogenation (O–H) and Brønsted acid-catalyzed cascade oxy-Michael–dehydration (OM–DH) of 1,3-diones, salicylic aldehydes and organic-hydrides is developed in one-pot to furnish the highly functionalized 3,9-dihydro-2H-cyclopenta[b]chromen-1-ones and 3,3-dimethyl-2,3,4,9-tetrahydro-xanthen-1-ones with high yields.