Abstract:The wide occurrence of pyrroles in natural products and pharmaceuticals calls for novel synthetic methodologies for the efficient synthesis of enantiopure pyrroles. Owing to their highly reactive nature and wide-ranging chemical landscape, enormous efforts have been dedicated not only to their synthesis but also to the development of reactions using them as a platform and their utilization in the stereocontrolled synthesis of diverse molecules. In sharp contrast to the extensive studies devoted toward indoles,… Show more
“…Moreover, alkylated pyrazines are used as flavoring agents in the food industry due to their strong aromatic properties, while methoxylated pyrazines in the perfume industry are used to improve the odor of cosmetics and toiletries [ 19 ]. On the other hand, pyrrole and its derivatives have been proved to play a significant role in material science, as a component of optoelectronic equipment, and in pharmaceutical chemistry, since several pyrrole-based drugs have been discovered [ 20 ]. The nitrogen compounds’ contribution to the total volatile fingerprint is similar between the spent coffee grounds from Ethiopia and Brazil, 33.27 and 32.72%, respectively.…”
Coffee is one of the most popular beverages worldwide, whose production and consumption result in large amounts of waste, namely spent coffee grounds, constituting an important source of compounds for several industrial applications. This work focused on the establishment of the volatile fingerprint of five spent coffee grounds from different geographical origins using headspace solid-phase microextraction coupled with gas chromatography-mass spectrometry (HS-SPME/GC-MS), as a strategy to identify volatile organic metabolites (VOMs) with potential application in the food industry as antioxidant, anti-inflammatory, and antiproliferative agents. One hundred eleven VOMs belonging to different chemical families were identified, of which 60 were found in all spent coffee grounds analyzed. Furanic compounds (34%), nitrogen compounds (30%), and esters (19%) contributed significant to the total volatile fingerprint. The data obtained suggest that spent coffee grounds have great potential to be used as raw material for different approaches in the food industry towards the development of new food ingredients or products for human consumption, in addition to pharmaceutical and cosmetic applications, namely as antioxidant (e.g., limonene, carvacrol), antimicrobial (e.g., pyrrole-2-carboxaldehyde, β-myrcene) and anti-inflammatory (e.g., furfural, 2-furanmethanol) agents, promoting their integral valorization within the circular bioeconomy concept.
“…Moreover, alkylated pyrazines are used as flavoring agents in the food industry due to their strong aromatic properties, while methoxylated pyrazines in the perfume industry are used to improve the odor of cosmetics and toiletries [ 19 ]. On the other hand, pyrrole and its derivatives have been proved to play a significant role in material science, as a component of optoelectronic equipment, and in pharmaceutical chemistry, since several pyrrole-based drugs have been discovered [ 20 ]. The nitrogen compounds’ contribution to the total volatile fingerprint is similar between the spent coffee grounds from Ethiopia and Brazil, 33.27 and 32.72%, respectively.…”
Coffee is one of the most popular beverages worldwide, whose production and consumption result in large amounts of waste, namely spent coffee grounds, constituting an important source of compounds for several industrial applications. This work focused on the establishment of the volatile fingerprint of five spent coffee grounds from different geographical origins using headspace solid-phase microextraction coupled with gas chromatography-mass spectrometry (HS-SPME/GC-MS), as a strategy to identify volatile organic metabolites (VOMs) with potential application in the food industry as antioxidant, anti-inflammatory, and antiproliferative agents. One hundred eleven VOMs belonging to different chemical families were identified, of which 60 were found in all spent coffee grounds analyzed. Furanic compounds (34%), nitrogen compounds (30%), and esters (19%) contributed significant to the total volatile fingerprint. The data obtained suggest that spent coffee grounds have great potential to be used as raw material for different approaches in the food industry towards the development of new food ingredients or products for human consumption, in addition to pharmaceutical and cosmetic applications, namely as antioxidant (e.g., limonene, carvacrol), antimicrobial (e.g., pyrrole-2-carboxaldehyde, β-myrcene) and anti-inflammatory (e.g., furfural, 2-furanmethanol) agents, promoting their integral valorization within the circular bioeconomy concept.
“…The construction of oxygen and nitrogen-containing heterocycles have always been attracted as a key fascinating area for organic synthesis owing to their widespread prevalence in the domain of drug design and developments, medicinal and pharmaceutical chemistry, as well as material sciences 30 – 32 . Chromene and their derivatives, particularly 2 H -chromene-2-one also known as coumarin 6 , and 2-amino-4 H -chromene 33 , possessing cyano functionality at the C-3 position, constitute such an imperative class of oxygen-containing heterocycles, which have potential therapeutic application in the treatment of diverse range disease manifestations such as Alzheimer’s disease, psoriatic arthritis, rheumatoid arthritis, amyotrophic lateral sclerosis, Parkinson’s disease, cancer therapy, as well as in Huntington’s disease.…”
Here, we have demonstrated a metal-free energy-efficient mechanochemical approach for expedient access to a diverse set of 2-amino-3-cyano-aryl/heteroaryl-4H-chromenes, tetrahydrospiro[chromene-3,4′-indoline], 2,2′-aryl/heteroarylmethylene-bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) as well as tetrahydro-1H-xanthen-1-one by employing the reactivity of 5,5-dimethylcyclohexane-1,3-dione/cyclohexane-1,3-dione with TsOH⋅H2O as Brønsted acid catalyst under water-assisted grinding conditions at ambient temperature. The ability to accomplish multiple C–C, C=C, C–O, and C–N bonds from readily available starting materials via a domino multicomponent strategy in the absence of metal-catalyst as well as volatile organic solvents with an immediate reduction in the cost of the transformation without necessitates complex operational procedures, features the significant highlights of this approach. The excellent yield of the products, broad functional group tolerances, easy set-up, column-free, scalable synthesis with ultralow catalyst loading, short reaction time, waste-free, ligand-free, and toxic-free, are other notable advantages of this approach. The greenness and sustainability of the protocol were also established by demonstrating several green metrics parameters.
“…The existence of organocatalyst has led to a revolution in the synthesis of molecular diversity and complexity in an asymmetric and non-asymmetric manner via several activation modes and has turned into one of the most important hot topics of current research in terms of synthetic efficiency and from the green chemistry point of view ( Dalko and Moisan, 2001 ; Barbas, 2008 ; MacMillan, 2008 ). The distinctive ability to accomplish chemical transformation through different activation modes, avoidance of expensive catalysts and metal catalyst(s), high stability, ready availability, easy recoverability, lower activation energy, high efficiency, and an immediate reduction in the toxicity and reaction costs offers organocatalytic synthetic approaches as efficient routes for the synthesis of a diverse range of quinazolinone scaffolds from the green and sustainable chemistry viewpoints ( Renzi and Bella, 2012 ; Ren and Wang, 2013 ; Borah et al, 2021d ).…”
Quinazolinone, a bicyclic compound, comprises a pyrimidine ring fused at 4´ and 8´ positions with a benzene ring and constitutes a substantial class of nitrogen-containing heterocyclic compounds on account of their frequent existence in the key fragments of many natural alkaloids and pharmaceutically active components. Consequently, tremendous efforts have been subjected to the elegant construction of these compounds and have recently received immense interest in synthetic and medicinal chemistry. The domain of synthetic organic chemistry has grown significantly over the past few decades for the construction of highly functionalized therapeutically potential complex molecular structures with the aid of small organic molecules by replacing transition-metal catalysis. The rapid access to this heterocycle by means of organocatalytic strategy has provided new alternatives from the viewpoint of synthetic and green chemistry. In this review article, we have demonstrated a clear presentation of the recent organocatalytic synthesis of quinazolinones of potential therapeutic interests and covered the literature from 2015 to date. In addition to these, a clear presentation and understanding of the mechanistic aspects, features, and limitations of the developed reaction methodologies have been highlighted.
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