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Free-radical reaction
About: Free-radical reaction is a research topic. Over the lifetime, 1919 publications have been published within this topic receiving 56787 citations.
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05 Mar 2014
TL;DR: In this article, a chemical synthesizing method of ozagrel is presented, which comprises the following steps: carrying out a free radical reaction on p-tolualdehyde and 1, 3-dibromo-5, 5-dimethylhydantoin (DBDMH) in an organic solvent under the effect of an initiator at 40-90 DEG C to obtain 4-bromo methyl benzaldehyde; then, carrying out an intermediate step on 4-mixture benzaldehyde and imidazole in a dipolar aprotic
Abstract: The invention discloses a chemical synthesizing method of ozagrel. The method comprises the following steps: carrying out a free radical reaction on p-tolualdehyde and 1, 3-dibromo-5, 5-dimethylhydantoin (DBDMH) in an organic solvent under the effect of an initiator at 40-90 DEG C to obtain 4-bromo methyl benzaldehyde; then, carrying out a reaction on 4-bromo methyl benzaldehyde and imidazole in a dipolar aprotic solvent at a room temperature under the effect of an accelerant to obtain 4-(1-imidazole methyl) benzaldehyde; and carrying out a reaction on 4-(1-imidazole methyl) benzaldehyde and acetic anhydride in an eutecticevaporate solvent to obtain ozagrel. Compared with conventional synthetic methods, the method disclosed by the invention is available in raw materials and low in cost of raw materials, short in reaction step, free from column chromatography isolation, low in preparation method and less in three-waste emission. The method disclosed by the invention is suitable for industrially producing ozagrel.
TL;DR: In this article , a photoredox three-component reaction of α-acyloxy-N-heterocycles as radical precursors, styrene derivatives as radical trapping agents, and alcohols as nucleophilic quenchers is presented.
Abstract: The Spin-Center Shift (SCS) elimination is a specific way for the generation of radicals with relevance in synthetic and biochemical pathways. The combination of SCS-mediated radical chemistry and atom-transfer radical addition (ATRA) offers new directions in diversity-oriented chemical synthesis. Herein, we report a photoredox three-component reaction of α-acyloxy-N-heterocycles as radical precursors, styrene derivatives as radical trapping agents, and alcohols as nucleophilic quenchers. The novel radical-polar crossover reaction provides access to a diverse set of branched ethers possessing high structural complexity. The utility of the transformation was also demonstrated by the synthesis of a complex drug derivative and it was easily scalable to the multigram level. The scope and limitations were also explored and a plausible mechanism was proposed.
TL;DR: A radical bicyclization of 2-cyanoaryl acrylamides with dicumyl peroxide has been developed for constructing a broad spectrum of benzo[h]naphtho[1,8-bc][1,6] naphthyridine as discussed by the authors , which allows the formation of three new chemical bonds through addition of methyl radical across alkene double bond, intramolecular addition of carbon-centered radical to cyano group and cyclization of the iminyl radical cascade.
Abstract: A radical bicyclization of 2-cyanoaryl acrylamides with dicumyl peroxide has been developed for constructing a broad spectrum of benzo[h]naphtho[1,8-bc][1,6]naphthyridine. This reaction allows the formation of three new chemical bonds through addition of methyl radical across alkene double bond, intramolecular addition of carbon-centered radical to cyano group and cyclization of the iminyl radical cascade, and features simple reaction system and wide substrate scope.
TL;DR: A photolytically generated ruthenium hydride species catalyzing a free radical cyclization reaction was developed in this article, where the new methodology ensures reproducibility of the free radical reaction of trialkyltin hydrides and a fast hydrogen transfer to the radical intermediates.
Abstract: A photolytically generated ruthenium hydride species catalyzing a free radical cyclization reaction was developed. As the new methodology ensures reproducibility of the free radical reaction of trialkyltin hydrides and a fast hydrogen transfer to the radical intermediates, the methodology provides fast quenching of radical intermediates and thus suppresses rearrangement of radical intermediates before the hydride quench. By offering new reactivity and selectivity to the trialkyltin hydride mediated free radical cyclization reactions, the methodology will find wide range of applications in organic synthesis.
01 Jan 2018
TL;DR: In this article, the phototriggered base proliferation and UV photopolymerization were introduced into thiol-ene reaction, which integrated the safety and strong penetrating ability of UV-based base proliferation reaction as well as Domino free radical photopolymersization based on phototrgered base reaction, is expected to expand the application of thiolene Michael addition reaction.
Abstract: Free radical reaction of thiol-ene photo click reaction is not ideal click chemistry type, there is monomer homopolymerization and low monomer conversion existing, as well as uncontrollable, it is difficult to obtain the target product. In this paper, the phototriggered base proliferation and UV photopolymerization were introduced into thiol-ene reaction. We synthesized photobase generator 2-(2-nitrophenyl) propyl oxycarbonyl-hexylamine (NPPOC-HA) and amine amplifier. NPPOC-HA has UV absorption above 300 nm, and photolysis products are amine and styrene, no free radical produced. Next, we used phototriggered amine proliferation initiated via UV light to control the thiol-ene click reaction, reducing side effects. RTIR was adopted to monitor infrared absorption peaks change of –SH and –C=C, integrating peak area to verify the equal proportion reaction of thiol-ene. UV phototriggered base proliferation reaction, which integrated the safety and strong penetrating ability of UV photopolymerization as well as Domino free radical photopolymerization based on phototriggered base proliferation reaction, is expected to expand the application of thiol-ene Michael addition reaction.