Synthetic Communications An International Journal for Rapid Communication of Synthetic Organic Chemistry Diversity-oriented expedient route for the synthesis of 3-tetrahydropyrimidinyl-coumarins via MCR (original) (raw)
Related papers
An overview on synthetic strategies to coumarins
Synthetic Communications, 2018
Coumarins units have recently emerged as a hot topic of research due to their diverse applications. Their synthesis is partly based on classical methodologies such as Pechmann reaction or Knoevenagel condensation, but it also sparked the discovery of completely new pathways. In very recent years so-called vertically expanded coumarins were synthesized, effectively expanding the portfolio of existing architectures. This review serves as a guide through synthesis strategies to coumarins.
Overview on developed synthesis procedures of coumarin heterocycles
Journal of the Iranian Chemical Society
Considering highly valuable biological and pharmaceutical properties of coumarins, the synthesis of these heterocycles has been considered for many organic and pharmaceutical chemists. This review includes the recent research in synthesis methods of coumarin systems, investigating their biological properties and describing the literature reports for the period of 2016 to the middle of 2020. In this review, we have classified the contents based on co-groups of coumarin ring. These reported methods are carried out in the classical and non-classical conditions particularly under green condition such as using green solvent, catalyst and other procedures.
Original and Innovative Advances in the Synthetic Schemes of Coumarin-Based Derivatives: A Review
Systematic Reviews in Pharmacy, 2020
Coumarin, a chemical nucleus, is award gifted from nature. This description is due to the versatile of its derivatives and the wide variety of their biological activities. Although many coumarins have been originally isolated from natural origins, there is a mounting interest in the past decades to synthesize the coumarins in the laboratory. Many synthetic routes have been documented named Perkin, Wittig, Pechmann, Claisen, Reformatsky, and Knoevenagel pathways. To maximize the yield, reduce the reaction period, minimize the side products, and make these reactions environmentally friend, several innovative approaches have been developed. These include the use of ultrasound, microwave, and solvent-free conditions to satisfy these goals. This review was focused on the traditional synthetic routes of coumarins and their innovative improvements as well as the benefits arising from the use of each of them.
Synthesis of 4-(2-hydroxymethylaryl)coumarins
Russian Chemical Bulletin, 2010
New 4 (2 hydroxymethylaryl)coumarins were prepared using the Suzuki-Miyaura cross coupling at the key step. According to X ray diffraction data, the compounds obtained are structural analogs of the natural stilbene combretastatin A 4, which exhibits potent antitumor activity.
Tetrahedron Letters, 2009
O-Methyl-4-coumarincarbaldehyde oxime reacted as an azadiene with electron-deficient and electronrich dienophiles to give, via one-step hetero-Diels-Alder cycloaddition reactions, the corresponding 5H-coumarin[4,3-c]pyridin-5-ones. When excess of the dienophile was used, fused azatetracyclo derivatives were also formed via a tandem Diels-Alder and 1,3-dipolar cycloaddition reaction of the dienophile to an azomethine ylide formed by the intermediate 2,3-dihydro-5H-coumarin[4,3-c]pyridine-5-one. The regio-and stereoselectivities of the new compounds correspond well with spectroscopic (2D NMR) and theoretical data. A possible mechanistic scheme is provided.
Classical Approaches and Their Creative Advances in the Synthesis of Coumarins: A Brief Review
Journal of Medicinal and Chemical Sciences, 2021
Coumarin chemical nucleus is a gift awarded from nature to humanity. The multifarious derivatives and the broad range of their bio-medicinal potentials are the basis for this description. In the last several decades, though numerous coumarin-based products have been primarily separated from their biological origins, the laboratory synthesis of the coumarins is developing. Various synthetic trails namely Knoevenagel, Claisen, Perkin, Pechmann, Wittig, and Reformatsky have been reported. Several advanced innovations have been created to maximize yield, minimize overall reaction time, avoid side products, and make synthetic reactions environmentally friendly. These include the employment of ultrasonic, microwave, and solventfree conditions. This brief review focuses on the classic methods for synthesizing coumarins, and the advantages derived from the use of creative catalytic tools.
ChemInform, 2014
A one-pot green protocol involving four-components in aqueous medium is developed to synthesize highly-functionalized pyrroles in good yields. Two of the newly synthesized compounds were subjected to in silico analysis on the Pharm Mapper web-server and the human mitogen-activated protein kinase1 (MEK1) enzyme was identified as a potential target protein for these compounds. For target validation, MEK-1 inhibition was performed with two representative compounds (5g and 5h) using docking simulations. These functionalized pyrroles were also tested for their respective IC 50 values on human cancer cell lines to evaluate their biocompatibility. Several of these functionalized pyrrole molecules were found to possess higher growth inhibition activity than standard doxorubicin and cisplatin. † Electronic supplementary information (ESI) available: Spectra of multisubstituted pyrrole derivatives 5a-j.
Functionalized 4Hydroxy Coumarins: Novel Synthesis, Crystal Structure and DFT Calculations
Molecules, 2011
A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-cyclization process under mild reaction conditions. The structure of 3-methoxycarbonyl-4-hydroxy coumarin has been established by X-ray diffraction analysis and its geometry was compared with optimized parameters by means of DFT calculations.