Synthesis of N-Substituted Pyrroles Catalyzed by Low-Cost and Commercially Available Aluminas

PORTILLA-ZÚÑIGA, OMAR; BAUTISTA-AGUILERA, ÓSCAR M.; MARTÍNEZ, JOSÉ J.; ROJAS, HUGO; MACÍAS, MARIO A.; IRIEPA, ISABEL; PÉREZ-REDONDO, ADRIÁN; SATHICQ, ÁNGEL; CASTILLO, JUAN-CARLOS; ROMANELLI, GUSTAVO P.

Catalysts

MDPI

Año: 2023 vol. 13

The Paal-Knorr reaction of acetonylacetone with primary amines catalyzed by CATAPAL 200 under conventional heating at 60 °C for 45 min afforded N-substituted pyrroles in 68–97% yields. The pyrrole 3g was studied by single-crystal and powder X-ray diffraction. The high percentage of Brønsted–Lewis acid sites (23%) and pore diameter (37.8 nm) of CATAPAL 200 favor the formation of the pyrrole ring because an increase in Brønsted acid sites efficiently catalyzes condensation and dehydration processes. This protocol is distinguished by its operational simplicity, high yields, reduced reaction time, no solvent required, stoichiometric amounts of reactants, low catalyst loading, and clean reaction profile. In addition, the CATAPAL 200 is cheap and commercially available leading to an efficient and lower-cost chemical transformation. The reusability of the catalyst for up to five cycles without appreciable loss of its catalytic activity makes the present protocol sustainable and advantageous compared to conventional methods.