613-46-7Relevant articles and documents
Photocycloaddition of Cyanonaphthalenes to 1,3-Cyclohexadiene
Noh, Taehee,Kim, Daekyun,Kim, Yong-Jae
, p. 1212 - 1216 (1998)
To prevent secondary processes due to facile thermal reaction, low-temperature irradiations of cyanonaphthalenes and 1,3-cyclohexadiene through a Pyrex filter were conducted. Along with the identification of the products, the results of the triplet-sensitized photoreaction of the irradiated mixture, low-temperature 1H NMR study of the irradiated mixture, and the Cope rearrangement reaction of some products suggested that the primary major products are the corresponding exo-[4 + 4] adducts fused at 1,4 position of the naphthalene skeleton and the syn-[2 + 2] adducts fused at 1,2 position. The formations of the primary products in these singlet-state photocycloaddition reactions were interpreted by primary and secondary orbital interactions. A rationalization for the previous results on the photoreactions at room temperature was also provided.
β-naphthalene incorporated thiazole-5-carboxamides/thiazole -5- ketones: Design, synthesis and anticonvulsant screening against two seizure models
Arshad, Mohammed Faiz,Al-Otaibi, Faisal,Mustafa, Gulam,Shousha, Saad,Alshahrani, Abdulrahman
, p. 27 - 37 (2019)
A bunch of β-naphthalene incorporated thiazole-5-carboxamides/thiazole -5- ketones (7a-7o& 8a-8e) were prepared by reacting 4-methyl-2-(naphthalen-2-yl)thiazole-5-carbonyl chloride with appropriate amines. Structures of all the compounds were explained by elemental analysis, FT-IR, 1H NMR and mass spectral data. The compounds were evaluated for their anticonvulsant activity employing MES and chemoshock (scPTZ) seizure tests. Neurotoxicity was also assessed. Majority of these compounds exhibited significant activity against both animal models; however, compounds 7e, 7j, 7n and 8c displayed promising activity and could be considered as leads for further investigations.
Photoinduced Electron Transfer Reaction of Mono- and Dicyanonaphthalenes with Allyltrimethylsilane: Synthesis of Benzotricyclo3,8>nonenes by Reductive Photoallylation and Intramolecular (2? + 2?) Photocycloaddition
Nishiyama, Toshinori,Mizuno, Kazuhiko,Otsuji, Yoshio,Inoue, Hiroo
, p. 6695 - 6706 (1995)
Irradiation of an acetonitrile-methanol (4:1) solution containing 1-cyanonaphthalene and allyltrimethylsilane (1) through Pyrex filter (>280 nm) regioselectively gave 3-cyano-4,5-benzotricyclo3,8>-4-nonene.The photoreaction of 2-cyanonaphthalene, 1-cyano-2-methylnaphthalene, 1-cyano-4-methylnaphthalene, 1,5- and 2,3-dicyanonaphthalenes with 1 gave the corresponding benzotricyclic compounds also in a regioselective manner.However, the photorection of 2,3-disubstituted 1,4-dicyanonaphthalenes with 1 gave no benzotricyclic compounds, but only the allyl substitution and reductive allylation products.These photoreactions were initiated by photoinduced electron transfer from 1 to the excited singlet states of mono- and dicyanonaphthalenes.The reductive allylation products from the former cyanonaphthalenes afforded the benzotricyclic compounds by an intramolecular (2? + 2?) photocycloaddition in good yields.The regioselectivity in the allylation reaction is discussed on the basis of the results of MO calculations of the radical anions of mono- and dicyanonaphthalenes.
Concentration-dependent isotope effects. The photocyanation of naphthalene
Zuilhof, Han,Van Gelderen, Frans A.,Cornelisse, Jan,Lodder, Gerrit
, p. 5456 - 5464 (1998)
Concentration-dependent isotope effects (IEs) were measured in the competitive photocyanation of naphthalene and perdeuterionaphthalene in acetonitrile in the presence of electron acceptors. The concentration of the reagents naphthalene, cyanide, and oxygen influences the magnitude of the IE. Experiments in which the photocyanation is brought about via selective excitation of an electron acceptor show that the naphthalene-concentration dependence of the IEs is not caused by the naphthalene radical cations, which are intermediates in the photoreaction. This is corroborated by an electrochemical study of (the reactivity of) these radical cations. From these observations and complementary semiempirical PM3 calculations it is concluded that the variation of the IE with naphthalene concentration is due to an excited-state equilibration. A detailed reaction mechanism is proposed to account for the observed IEs.
Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones
Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki
supporting information, p. 3799 - 3802 (2022/04/07)
The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.
Cyanide-Free Cyanation of Aryl Iodides with Nitromethane by Using an Amphiphilic Polymer-Supported Palladium Catalyst
Niimi, Ryoko,Suzuka, Toshimasa,Uozumi, Yasuhiro
supporting information, p. 40 - 44 (2021/11/30)
A cyanide-free aromatic cyanation was developed that uses nitromethane as a cyanide source in water with an amphiphilic polystyrene poly(ethylene glycol) resin-supported palladium catalyst and an alkyl halide (1-iodobutane). The cyanation proceeds through the palladium-catalyzed cross-coupling of an aryl halide with nitromethane, followed by transformation of the resultant (nitromethyl)arene intermediate into a nitrile by 1-iodobutane.
CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source
Ren, Yun-Lai,Shen, Zhenpeng,Tian, Xinzhe,Xing, Ai-Ping,Zhao, Zhe
, (2020/10/26)
Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.
Development of Potent 3-Br-isoxazoline-Based Antimalarial and Antileishmanial Compounds
Galbiati, Andrea,Zana, Aureliano,Coser, Consuelo,Tamborini, Lucia,Basilico, Nicoletta,Parapini, Silvia,Taramelli, Donatella,Conti, Paola
supporting information, p. 1726 - 1732 (2021/11/01)
Starting from the structure of previously reported 3-Br-isoxazoline-based covalent inhibitors of P. falciparum glyceraldehyde 3-phosphate dehydrogenase, and with the intent to improve their metabolic stability and antimalarial activity, we designed and synthesized a series of simplified analogues that are characterized by the insertion of the oxadiazole ring as a bioisosteric replacement for the metabolically labile ester/amide function. We then further replaced the oxadiazole ring with a series of five-membered heterocycles and finally combined the most promising structural features. All the new derivatives were tested in vitro for antimalarial as well as antileishmanial activity. We identified two very promising new lead compounds, endowed with submicromolar antileishmanial activity and nanomolar antiplasmodial activity, respectively, and a very high selectivity index with respect to mammalian cells.
Efficient nitriding reagent and application thereof
-
Paragraph 0239-0241, (2021/03/31)
The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
Novel chalcone/aryl carboximidamide hybrids as potent anti-inflammatory via inhibition of prostaglandin E2 and inducible NO synthase activities: design, synthesis, molecular docking studies and ADMET prediction
Ibrahim, Tarek S.,Moustafa, Amr H.,Almalki, Ahmad J.,Allam, Rasha M.,Althagafi, Abdulhamid,Md, Shadab,Mohamed, Mamdouh F. A.
, p. 1067 - 1078 (2021/05/28)
Two series of chalcone/aryl carboximidamide hybrids 4a–f and 6a–f were synthesised and evaluated for their inhibitory activity against iNOS and PGE2. The most potent derivatives were further checked for their in?vivo anti-inflammatory activity utilising carrageenan-induced rat paw oedema model. Compounds 4c, 4d, 6c and 6d were proved to be the most effective inhibitors of PGE2, LPS-induced NO production, iNOS activity. Moreover, 4c, 4d, 6c and 6d showed significant oedema inhibition ranging from 62.21% to 78.51%, compared to indomethacin (56.27 ± 2.14%) and celecoxib (12.32%). Additionally, 4c, 6a and 6e displayed good COX2 inhibitory activity while 4c, 6a and 6c exhibited the highest 5LOX inhibitory activity. Compounds 4c, 4d, 6c and 6d fit nicely into the pocket of iNOS protein (PDB ID: 1r35) via the important amino acid residues. Prediction of physicochemical parameters exhibited that 4c, 4d, 6c and 6d had acceptable physicochemical parameters and drug-likeness. The results indicated that chalcone/aryl carboximidamides 4c, 4d, 6c and 6d, in particular 4d and 6d, could be used as promising lead candidates as potent anti-inflammatory agents.
