ZrCl4 as an efficient catalyst for one-pot four-component synthesis of polysubstituted dihydropyrrol-2-ones

Abstract

An efficient synthesis of polysubstituted dihydropyrrol-2-one derivatives via one-pot four-component domino reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of zirconium tetrachloride (ZrCl 4 ) is described. The presented methodology offers several advantages such as simplicity of operation, good to high yields, short reaction times, inexpensive and readily available starting material and catalyst. Furthermore, the products were obtained through simple filtering with no need for column chromatography. Graphical abstract Keywords Heterocycle Á Dihydropyrrol-2-one Á ZrCl 4 Á Dialkyl acetylenedicarboxylate Á Multi-component reaction Electronic supplementary material The online version of this article (

Al2(SO4)3·18H2O as an Eco-Safe Catalyst Promoting Synthesis of Polysubstituted Dihydropyrrol-2-ones

“…In the past decades, considerable attention has been paid to the design of efficient and environmental friendly synthetic route by using of multi-component reactions (MCRs) [10][11][12][13][14][15][16][17] due to a wide range of points, such as atom-economy, simple work-up, mildness and environmental friendliness, one pot, and low cost. Due to the importance of polysubstituted dihydropyrrol-2-ones, various methodologies for the preparation of these 1 School of Engineering, Apadana Institute of Higher Education, Shiraz, Iran * Mohamadpour.f.7@gmail.com Ó Mohamadpour F., 2020 compounds have been developed, such as Cu(OAc) 2 •H 2 O [18], InCl 3 [19], I 2 [20], AcOH [21], [n-Bu 4 N][HSO 4 ] [22], Al(H 2 PO 4 ) 3 [23], oxalic acid [24], ZrCl 4 [25], [Hpyro][HSO 4 ] [26], and p-TsOH•H 2 O [27] can be used as catalysts for this transformation. Some of these methodologies have limitations such as long reaction time, low yields, toxic and expensive catalysts, complex workup, and use of strongly acidic conditions.…”

Glutamic acid as green and bio-based α-amino acid catalyst promoted one-pot access to polyfunctionalized dihydro-2-oxypyrroles

“…To date, a number of methodologies have been reported for the preparation of these compounds that included various catalysts such as I 2 , 8 InCl 3 , 9 [n-Bu 4 N][HSO 4 ], 10 Al(H 2 PO 4 ) 3 , 11 AcOH, 12 Cu(OAc) 2 ⋅H 2 O, 13 oxalic acid dihyd-1084 MOHAMADPOUR rate, 14 ZrCl 4 , 15 2,6-pyridinedicarboxylic acid, 16 Fe 3 O 4 @nano-cellulose-OPO 3 H 17 and ethylenediammonium diformate (EDDF). 18 Some of these methods have limitations such as long reaction times, low yields and the use of strongly acidic conditions, high temperature, difficult work-up, toxic and expensive catalysts.…”

Caffeine as a naturally green and biodegradable catalyst promoted convenient and expedient synthetic route for the synthesis of polysubstituted dihydro-2-oxypyrroles

“…Some of them with biological properties have been shown in Figure 1. To date, methods for the synthesis of high substituted dihydro-2-oxypyrroles have been reported using MCRs in the presence of various catalysts such as I 2 [11], InCl 3 [12] [14], AcOH [15], Cu(OAc) 2 .H 2 O [16], oxalic acid dihydrate [17], ZrCl 4 [18] and Fe 3 O 4 @nano-cellulose-OPO 3 H [19]. Some of these methods have limitations such as long time reactions, low yields, the use of strongly acidic conditions, high temperature, difficulty work-up, toxic and expensive catalysts.…”