Access of Diverse 2-Pyrrolidinone, 3,4,5-Substituted Furanone and 2-Oxo-dihydropyrroles Applying Graphene Oxide Nanosheet: Unraveling of Solvent Selectivity

Abstract

Eco benign catalyst graphene oxide (GO) has been effectively exploited in one pot synthesis of 2‐pyrrolidinone, 3,4,5‐substituted furanone and 2‐oxodihydropyrrole derivatives, three important pharmacophores, via one‐pot domino reactions (MCR) among easily accessible amines, aldehydes and acetylinic esters. These small heterocyclic molecules have been well diversified employing a wide variety of amines and aldehyde derivatives establishing the broad catalytic activity of graphene oxide towards the synthesis of three potential pharmacophores in good to excellent yields. The protocol features inherent solvent selectivity generating two different heterocyclic core (2‐pyrrolidinone and 3,4,5‐substituted furanones) starting from common substrates under similar reaction condition. This carbocatalyst prompted protocol demonstrates a rapid and efficient route for the design of biologically diverse heterocycles under mild condition.

A Brønsted Acid-Catalyzed Multicomponent Reaction for the Synthesis of Highly Functionalized γ-Lactam Derivatives

“…In this case, the nucleophilic addition of aromatic amines to the activated alkyne gives rise to a deactivated enamine intermediate and 0.5 equivalents of benzoic acid are required in order to promote the subsequent Mannich reaction [30]. Activation of this process was also described by the use of molecular iodine [31] or graphene-oxide nanosheets under solvent-free conditions [32]. In this context, organocatalysis is identified to be at the heart of greening of chemistry, because this branch of science is found to reduce the environmental impact of chemical processes.…”

Efficient and Eco‐Friendly One‐Pot Synthesis of Functionalized Furan‐2‐one, Pyrrol‐2‐one, and Tetrahydropyridine Using Lemon Juice as a Biodegradable Catalyst

“…Previously, furan‐2‐ones have been prepared by employing β‐cyclodextrin, SnCl 2 .2H 2 O, ZnO nanoparticles, [Bu 4 N][HSO 4 ], sucrose, N ‐methyl 2‐pyrrolidonium hydrogen sulfate ([ H ‐NMP]HSO 4 ), SnO nanoparticles, HY Zeolite nano‐powder, watermelon juice, barberry juice, Vitamin B12, and graphene oxide (GO) as catalysts. Moreover, for the synthesis of pyrrol‐2‐ones, literature shows several methods with different catalysts which include acetic acid, I 2 , 1‐methyl‐2‐oxopyrrolidinium hydrogen sulfate ([Hpyro][HSO 4 ]), Cu(OAc) 2 ⋅H 2 O, TiO 2 nanopowder, trityl chloride, [n‐Bu 4 N][HSO 4 ], InCl 3, (S)‐camphorsulfonic acid, nanoZnO, vitamin B12, ethylenediammoniumdiformate (EDDF), 2,6‐pyridinedicarboxylic acid, UiO‐66‐SO 3 H metal‐organic framework, magnetic metal‐organic framework‐based catalyst CoFe 2 O 4 @SiO 2 @IRMOF‐3, Fe 3 O 4 @nano‐cellulose‐OPO 3 H, N,N,N,N ‐tetramethyl guanidinium acetate [TMG][Ac], graphene oxide (GO) etc . Despite the effectiveness of these catalysts, the usage of some of these methods are allied with several short comings such as harsh reaction conditions,, use of stoichiometric amounts of catalysts, prolonged reaction time,,,, difficulty in product isolation,,, and co‐occurrence of side reactions.…”

N-tert-Butyl-2-{2-[2-(4-chlorophenyl)-4-hydroxy-1-(5-methylisoxazol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrol-3-yl]-N-(4-methoxyphenyl)acetamido}-2-(4-methoxyphenyl)acetamide methanol monosolvate: single-crystal X-ray diffraction study and Hirshfeld surface analysis

“…A search of the Cambridge Structural Database (CSD Version 5.42, update of November 2020; Groom et al, 2016) for the 3hydroxy-1,5-dihydro-pyrrol-2-one fragment revealed 79 hits. Only 27 of these hits contain a fragment with the same structure as that of the title compound [refcodes: BOQXEN (del Corte et al, 2019), CIKPAQ (Sarkar et al, 2018), EVIYUD (Aliev et al, 2003b), GEJZAY (Mashevskaya et al, 2011), GIMGEQ (Sarkar et al, 2013), GITCAQ, GITDEV (Saha et al, 2017), IRUBUS (Aliev et al, 2003a), LIFBEJ, LIFBOT (Sun et al, 2011), NUXPIG (Wiedemann et al, 2009), PADHUA (Zonouz et al, 2015), PASTOT (Nicolaou et al, 2005), QIPNAH (Bhajammanavar et al, 2019), ROHNAG (Hosseinzadeh et al, 2019), TOMPER (Sakhno et al, 2008), UJEXOY (Ahankar et al, 2016), VILQEP (Gein et al, 2018), VIPNAJ (Mylari et al, 1991), VIQDOP (Guseinov et al, 2006), VOWGAP (Kazakov et al, 1990), WAPMIM (Dubovtsev et al, 2016), XINHIL (Aliev et al, 2001), XOKRAT, XOKRAT01 (Ramazani et al, 2019), YAJMOM (Wei et al, 2004), YIYFAP (Denislamova et al, 2014)]. All these structures and the title compound have the same electron density distribution within the 3-hydroxy-1,5-dihydropyrrol-2-one fragment.…”