A green method for the synthesis of pyrrole derivatives using arylglyoxals, 1,3-diketones and enaminoketones in water or
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ORIGINAL ARTICLE
A green method for the synthesis of pyrrole derivatives using arylglyoxals, 1,3‑diketones and enaminoketones in water or water–ethanol mixture as solvent Mohammad Anary‑Abbasinejada1 · Frershteh Nezhad‑Shshrokhabadi1 · Marziyeh Mohammadi1 Received: 5 May 2019 / Accepted: 31 July 2019 © Springer Nature Switzerland AG 2019
Abstract Three-component reaction between arylglyoxals, 1,3-dicetones and enaminoketones leads to new polyfunctionalized tetraone derivatives which may be easily converted to polyfunctionalized pyrroles. Reactions were conducted in water or water–ethanol mixture as green solvents, and all products were isolated by simple washing of the resulting solids with diethyl ether. Graphic abstract O
HO
R3
O
O O Ar
O
OH
R3
R2
OH
H2O
R2 Ar
O
R2
O
R O 3
H2O-EtOH (1:1) 25oC
N
5'd-i
5a-c R2 O
O HN
reflux
O
R2 Ar
N
R3
N(Et)3 (10 mol%)
Ar
Me
O
O
R2
R3 O
NaOH (10 mol%) O
HN
4a-i R2
H2O-EtOH (1:1) reflux
Ar
N
6a-m Ar= 2-Thiophen, 4-Me-Ph, 4-Cl-Ph, 4-OMe-Ph, 4-NO2-Ph, 3-NO2-Ph, 4-Br-Ph, 2-Naphthyl, Ph R3=R2= Me, ph
R2
Keywords Pyrrole · Arylglyoxal · Enaminoketone · Green solvent · 1,3-diketones
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11030-019-09984-x) contains supplementary material, which is available to authorized users. * Mohammad Anary‑Abbasinejada [email protected] 1
Department of Chemistry, Vali-e-Asr University, Rafsanjan 77176, Iran
Pyrrole and its derivatives are among the most important nitrogen-containing heterocyclic compounds which exist in the structure of many natural products including bile pigments, heme, cytochromes, vitamin B12 and alkaloids [1, 2]. Pyrrole compounds are reported active as antibacterial [3], antioxidant [4], anti-inflammatory [5], antitubercular [6] and antitumor [7] drugs including BM212 (mycobacterium),
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atorvastatin (a cholesterol-lowering agent) and anthelmintic pyrvinium (nonsteroidal anti-inflammatory drugs) [8–12]. So, there is a continuous effort for the construction of functionalized pyrroles. The most commonly used methods for the synthesis of pyrrole derivatives include the Knorr synthesis [13], Hantzsch synthesis [14], Buchwald–Hartwig coupling [15] and Paal–Knorr condensation reaction [16]. However, many other comprehensive efforts, especially those using multi-component reactions, have been made toward the synthesis of a wide range of pyrrole-containing organic molecules [17–20]. Arylglyoxals with a carbonyl group adjacent to the aldehyde functionality are reactive and versatile species which have been widely used for the synthesis of different heterocyclic and carbocyclic compounds [21–23]. Multi-component reactions of arylglyoxals and enaminocarbonyl compounds have been recently used for the synthesis of a variety of polyfunctionalized pyrrole derivatives [24–34]. An important criterion of green chemistry is replacing hazardous organic solvents with environmentally favorable solvents. On the other hand
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