Naturally occurring organic acids for organocatalytic synthesis of pyrroles via Paal–Knorr reaction

Research on Chemical Intermediates - In this study, common naturally occurring organic acids, namely oxalic, malonic, succinic, tartaric and citric acid (as safe, inexpensive, and biodegradable...     

Vitamin B1 as a metal-ion-free natural catalyst for sustainable quinoxaline ring condensation under sonochemical conditions

Abstract  

The role of vitamin B₁ as a catalyst is investigated for the quinoxaline ring condensation under various mild reaction conditions. The results revealed that the combination of vitamin B₁ and ultrasonic irradiation promotes the reaction more efficiently. The salient features of this environmentally benign method are fast conversions, excellent yields for a wide range of substrates, and the use of a low-cost, readily available, nontoxic, and metal-ion-free natural catalyst. The wide range of turnover frequency values (6–400 h⁻¹) shows that the reaction rate is highly dependent on the nature of the functional groups on the aromatic ring of substrates. Moreover, a plausible mechanism for the catalytic action of vitamin B₁ has been introduced.     

<Emphasis Type="SmallCaps">l</Emphasis>-Tryptophan-catalyzed Paal–Knorr pyrrole cyclocondensation: an efficient,clean and recyclable organocatalyst

A simple, clean, and efficient solvent-free protocol is introduced for Paal–Knorr pyrrole synthesis catalyzed by l-tryptophan as a thermally resistant, natural primary amino acid. The products were obtained mostly in excellent yields through the reaction of hexane-2,5-dione with aromatic primary amines bearing a variety of substituents. The catalyst could be easily isolated from the reaction mixture and recycled at least six times without significant loss of activity. The procedure has an environmentally benign nature in agreement with the concepts of green chemistry.     

Zirconium(IV) chloride as versatile catalyst for the expeditious synthesis of quinoxalines and pyrido[2,3-<Emphasis Type="Italic">b</Emphasis>]pyrazines under ambient conditions

Abstract  

Among the various transition metal chlorides, zirconium(IV) chloride was found to be an efficient catalyst for the rapid synthesis of a wide range of 2,3-dialkyl- and 2,3-diaryl-quinoxaline and pyrido[2,3-b]pyrazine derivatives in excellent yields at room temperature. The remarkable features of this catalytic process are the mild reaction conditions, quantitative yields, short reaction times, high conversions, tolerability of various functional groups, clean reaction profiles, and operational simplicity.