2019
DOI: 10.4314/bcse.v33i1.15
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Caffeine as a naturally green and biodegradable catalyst promoted convenient and expedient synthetic route for the synthesis of polysubstituted dihydro-2-oxypyrroles

Abstract: A green, convenient, high yielding and one-pot procedure for synthesis of high substituted dihydro-2-oxypyrroles by domino four-component condensation reaction between aromatic/aliphatic amines, dialkyl acetylenedicarboxylate and formaldehyde in the presence of a catalytic amount of caffeine as a green, natural, expedient and biodegradable catalyst under ambient temperature was studied. The salient features of this green approach are simplicity of operation and work-up procedures with no necessity of chromatog… Show more

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Cited by 15 publications
(7 citation statements)
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“… in the presence tartaric acid as a eco‐friendly and di‐functional Brønsted acid catalyst in methanol at room temperature (Table 1 , Entry 1), [22] in the presence of lactic acid as catalyst in ethanol at room temperature (Table 1, Entry 2), [23] using graphene oxide in ethanol at room temperature (Table 1, Entry 3), [24] in the presence of CF 3 CO 2 H (20 mol %) in methanol at room temperature (Table 1, Entry 4), [25] in the presence of citric acid in methanol at room temperature (Table 1, Entry 5), [26] using caffeine in methanol at room temperature (Table 1, Entry 6), [27] using ZnCl 2 (15 mol %) as a Lewis acid catalyst in methanol at room temperature (Table 1, Entry 7), [28] using formic acid as a natural green and bio‐based catalyst in methanol at room temperature (Table Figure 1, Entry 8), [29] in the presence of nano‐Fe 3 O 4 @SiO 2 / SnCl 4 in EtOH at 60 °C (Table 1, Entry 9), [30] and using [TMBSED][OMs] 2 (20 mol %) ethanol at room temperature (Table 1, Entry 10) [31] . using Zn(SO 4 ) 2 ⋅ 7H 2 O as catalyst, in methanol at room temperature (Table 1, Entry 11) [32] .…”
Section: Synthesis Of Five‐membered Rings With One Heteroatom Includingmentioning
confidence: 99%
“… in the presence tartaric acid as a eco‐friendly and di‐functional Brønsted acid catalyst in methanol at room temperature (Table 1 , Entry 1), [22] in the presence of lactic acid as catalyst in ethanol at room temperature (Table 1, Entry 2), [23] using graphene oxide in ethanol at room temperature (Table 1, Entry 3), [24] in the presence of CF 3 CO 2 H (20 mol %) in methanol at room temperature (Table 1, Entry 4), [25] in the presence of citric acid in methanol at room temperature (Table 1, Entry 5), [26] using caffeine in methanol at room temperature (Table 1, Entry 6), [27] using ZnCl 2 (15 mol %) as a Lewis acid catalyst in methanol at room temperature (Table 1, Entry 7), [28] using formic acid as a natural green and bio‐based catalyst in methanol at room temperature (Table Figure 1, Entry 8), [29] in the presence of nano‐Fe 3 O 4 @SiO 2 / SnCl 4 in EtOH at 60 °C (Table 1, Entry 9), [30] and using [TMBSED][OMs] 2 (20 mol %) ethanol at room temperature (Table 1, Entry 10) [31] . using Zn(SO 4 ) 2 ⋅ 7H 2 O as catalyst, in methanol at room temperature (Table 1, Entry 11) [32] .…”
Section: Synthesis Of Five‐membered Rings With One Heteroatom Includingmentioning
confidence: 99%
“…There have been some recent reports of polyfunctionalized dihydro-2-oxypyrroles being synthesized via multicomponent processes in the presence of various catalysts including as I 2 , 17 glycine, 18 AcOH, 19 Cu(OAc) 2 .H 2 O, 20 Fe 3 O 4 @nano-cellulose–OPO 3 H, 21 BiFeO 3 nanoparticles, 22 nano-Fe 3 O 4 @SiO 2 /SnCl 4 , 23 glutamic acid, 24 graphene oxide, 25 CoFe 2 O 4 @SiO 2 @IRMOF-3, 26 2,6-pyridinedicarboxylic acid, 27 saccharin, 28 tartaric acid, 29 lemon juice, 30 nano-H 3 PW 12 O 40 /Fe 3 O 4 @SiO 2 -Pr-Pi, 31 UiO-66-SO 3 H, 32 caffeine, 33 nano-TiCl 4 /SiO 2 , 34 Fe/MWCNTs, 35 trityl chloride 36 and EDDF. 37 These methods have resulted in metal catalyst limitations, expensive reagents, harsh reaction conditions, monotonous unacceptable yields, environmental risks, workup processes, and long reaction times.…”
Section: Introductionmentioning
confidence: 99%
“…There are several synthetic techniques that can be used to make polyfunctionalized dihydro-2-oxypyrroles such as methylene blue 26 , I 2 27 , glycine 28 , AcOH 29 , Cu(OAc) 2 ·H 2 O 30 , Fe 3 O 4 @nano-cellulose–OPO 3 H 31 , tartaric acid 32 , nano-Fe 3 O 4 @SiO 2 /SnCl 4 33 , glutamic acid 34 , graphene oxide 35 , caffeine 36 , 2,6-pyridinedicarboxylic acid 37 , saccharin 38 , BiFeO 3 nanoparticles 39 , and CoFe 2 O 4 @SiO 2 @IRMOF-3 40 . Consequently, there is a shortage of metal catalysts, high reagent costs, difficult reactions, and poor yields, which increases reaction duration and impacts waste management.…”
Section: Introductionmentioning
confidence: 99%