1969-73-9Relevant academic research and scientific papers
Exploring the Potential of 2-(2-Nitrophenyl)ethyl-Caged N-Hydroxysulfonamides for the Photoactivated Release of Nitroxyl (HNO)
Bharadwaj, Vinay,Brasch, Nicola E.,Rahman, Mohammad S.,Sampson, Paul,Seed, Alexander J.
, p. 16448 - 16463 (2021/12/06)
The emergence of nitroxyl (HNO) as a biological signaling molecule is attracting increasing attention. HNO-based prodrugs show considerable potential in treating congestive heart failure, with HNO reacting rapidly with metal centers and protein-bound and free thiols. A new class of 2-(2-nitrophenyl)ethyl (2-NPE)-photocaged N-hydroxysulfonamides has been developed, and the mechanisms of photodecomposition have been investigated. Three photodecomposition pathways are observed: The desired concomitant C-O/N-S bond cleavage to generate HNO, sulfinate, and 2-nitrostyrene, C-O bond cleavage to give the parent sulfohydroxamic acid and 2-nitrostyrene, and O-N bond cleavage to release a sulfonamide and 2-nitrophenylacetaldehyde. Laser flash photolysis experiments provide support for a Norrish type II mechanism involving 1,5-hydrogen atom abstraction to generate an aci-nitro species. A mechanism is proposed in which the (Z)-aci-nitro intermediate undergoes either C-O bond cleavage to release RSO2NHO(H), concerted C-O/N-S bond cleavage to generate sulfinate and HNO, or isomerization to the (E)-isomer prior to O-N bond cleavage. The pKa of the N(H) of the N-hydroxysulfonamide plays a key role in determining whether C-O or concerted C-O/N-S bond cleavage occurs. Deprotonating this site favors the desired C-O/N-S bond cleavage at the expense of an increased level of undesired O-N bond cleavage. Triplet state quenchers have no effect on the observed photoproducts.
Synthesis method of phenylacetaldehyde derivative
-
Paragraph 0041; 0046-0047; 0050, (2021/08/07)
The present invention discloses a synthesis method of phenylacetaldehyde derivative, a benzaldehyde derivative is adopted as a raw material, an intermediate 2-methoxyvinylphenyl derivative is obtained through synthesis, then the phenylacetaldehyde derivative is obtained through synthesis, and the substituent group R of the benzaldehyde derivative includes but is not limited to m-methyl, m-ethyl, m-nitrile group, p-methyl, o-methyl, o-nitro and 2, 6-dimethyl. The synthesis process is simple, synthesis conditions are mild, post-treatment is relatively simple, and industrial production is easy; the universality is good, and substrates with different functional groups are compatible; the yield is considerable, part of compounds are almost quantitatively converted, and the requirement of atom economy is met.
4H-PYRROLO[3,2-C]PYRIDIN-4-ONE DERIVATIVES
-
Page/Page column 93-94, (2020/11/03)
Compounds of formula (I) for use in the treatment or prophylaxis of a disease, which is a hyperproliferative disease and/or a disorder responsive to induction of cell death, selected from a haematological tumour, a solid tumour and/or metastases thereof, said tumour harbouring a mutant EGFR with exon 19 or 21 mutations, and their use as pharmaceuticals.
4H-PYRROLO[3,2-C]PYRIDIN-4-ONE DERIVATIVES
-
Page/Page column 85, (2019/05/15)
Compounds of formula (I) processes for their production and their use as pharmaceuticals.
Synthetic process of aromatic acetaldehyde compound
-
Paragraph 0063; 0067; 0068, (2017/11/30)
The invention provides a synthetic process of an aromatic acetaldehyde compound; the synthetic method includes forming a mixed solution via starting material A with N,N-dimethylformamide dimethyl acetal; continuously feeding the mixed solution into a continuous reactor to carry out enamination reaction to obtain enamide B, and discharging the enamide B from the continuous reactor during enamination reaction; preparing aromatic acetaldehyde compound C with the enamide B, wherein the starting material A has a structural formula shown as formula (1), the enamide B has a structural formula shown as formula (2), and the aromatic acetaldehyde compound C has a structural formula shown as formula (3). By continuously feeding the mixed solution of reaction materials into the reactor to carry out enamination reaction, enamination reaction is continuously performed; continuous production of aromatic acetaldehyde compounds is achieved, reaction time is shortened, and reaction efficiency is improved.
Synthesis of indolines via a SmI2 promoted domino nitro reduction-intramolecular aza-Michael reaction
Ramos, Josierika A. Ferreira,Araújo, Carolina S.,Nagem, Tanus J.,Taylor, Jason G.
, p. 54 - 58 (2015/01/30)
A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza-Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2-(2-nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This "one pot" strategy also permitted the expeditious synthesis of a 1,2,3,4-tetrahydroquinoline, whereas the seven-membered 2,3,4,5-tetrahydrobenzoazepines compounds were not formed under these reaction conditions.
Facile synthesis of indolines by a tandem nitro-reduction Aza Michael addition reaction
Ventura, Wellington Martins,Souza De Assis, Luiz Guilherme,Taylor, Jason Guy
, p. 2023 - 2029 (2013/10/22)
A diverse array of substrates are conveniently prepared by coupling diazonium salts to ethyl vinyl ether and subjecting the resultant aldehyde intermediate to a Wittig reaction to provide α,β-unsaturated esters with only one purification step. The cyclisation of 4-aryl-but-2-enoates is carried out in the presence of stoichiometric amounts of SnCl 22H2O and thus this one-pot strategy also permitted the expeditious synthesis of indolines in good yield. The Japan Institute of Heterocyclic Chemistry.
Continuous-flow synthesis of monoarylated acetaldehydes using aryldiazonium salts
Chernyak, Natalia,Buchwald, Stephen L.
supporting information; experimental part, p. 12466 - 12469 (2012/09/05)
Anilines and ethyl vinyl ether can be used as precursors for a process that is the synthetic equivalent of the α-arylation of acetaldehyde enolate. The reaction manifests a high level of functional group compatibility, allowing the ready preparation of a number of synthetically valuable compounds.
An unusual route to a quinoline 1-oxide via intramolecular addition of an enolate to an aromatic nitro group
Moreira, Nayara Da Rocha F.,De Oliveira, Tania T.,Nagem, Tanus J.,Taylor, Jason G.
scheme or table, p. 203 - 205 (2012/03/12)
A mixture of ethyl 4-(2-nitrophenyl)butenoates undergoes an unusual intramolecular cyclisation in the presence of a catalytic amount of potassium tert-butoxide. 2011 · Copyright by Walter de Gruyter.
