- Aryl Ether Syntheses via Aromatic Substitution Proceeding under Mild Conditions
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In this study, mild conditions for aromatic substitutions during the syntheses of aryl ethers were developed. In the reaction conditions, the choices of solvent, base, and the sequence for the addition of the reagents proved important. A wide variety of alcohols were used directly as nucleophiles and smoothly reacted with aryl chlorides that possessed either a nitro or a cyano group at either the ortho- or para-position. Controlled experiments we performed suggested that the reaction underwent a charge-transfer process mediated by a combination of DMF and tert-BuOK.
- Ando, Shin,Tsuzaki, Marina,Ishizuka, Tadao
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p. 11181 - 11189
(2020/10/12)
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- NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature
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Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study.
- Ahmed, Jasimuddin,Hota, Pradip Kumar,Maji, Subir,Mandal, Swadhin K.,Rajendran, N. M.
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supporting information
p. 575 - 578
(2020/01/29)
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- Oxadiazole o-phenoxy compound and application
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The invention discloses an oxadiazole o-phenoxy compound. A structure is shown as a formula I: (The formula is shown in the description). The compound in the formula I has an excellent nematode-killing effect and can be used as a nematode-killing agent fo
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Paragraph 0021; 0022; 0023; 0024
(2018/09/12)
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- Oxadiazole pyrazole compound and application thereof
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The invention provides an oxadiazole pyrazole compound. The structure of the oxadiazole pyrazole compound is as shown in Formula I. The compound has an insecticidal action and can serve as an insecticide for preventing and controlling plant insect pests o
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Paragraph 0021; 0022; 0023
(2018/09/08)
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- Preparation method of alkoxy benzamide
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The invention relates to a novel preparation method of alkoxy benzamide. Specifically, the method comprises steps as follows: chlorobenzonitrile is taken as a raw material and subjected to a reaction with alkaline substances in the presence of a catalyst, alkoxy benzoyl cyanide is generated and subjected to a hydrolysis reaction, and alkoxy benzamide is generated. The method has the advantages that the raw material is cheap and available, reaction conditions are mild, and postprocessing is convenient and simple.
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Paragraph 0022; 0024
(2017/08/24)
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- High diastereoselectivity in the yang photocyclization via remote hydrogen abstraction reaction
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1-Benzoyl-1-(o-alkoxyphenyl)cyclopropanes undergo Yang photocyclization to form dihydrobenzopyranols in a stereospecific manner. The cyclopropyl group at alpha position to carbonyls gives not only a bias in the most stable geometries of the starting ketones but also conformational restriction on geometries of biradical intermediates. More importantly, intramolecular hydrogen bonds seem to give an additional effect on conformational control of the biradical reactivity.
- Jang, Mi,Park, Bong Ser
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p. 1509 - 1514
(2016/10/09)
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- Two ways of preparing benzonitriles using BrCCl3-PPh3 as the reagent
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Benzamides were converted into benzonitriles with BrCCl3- PPh3-Et3N in CH2Cl2 in an Appel-type reaction. Benzaldoximes could be transformed to benzonitriles under identical conditions. It was found that the reaction system BrCCl3-(2 equiv.)PPh3 was also suitable for these transformations with PPh 3 replacing Et3N.
- Jasem, Yosef Al,Barkhad, Mohamed,Khazali, Mona Al,Butt, Hifsa Pervez,El-Khwass, Noha Ashraf,Azani, Mariam Al,Hindawi, Bassam Al,Thiemann, Thies
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- Alternative method for the synthesis of imidazo[5,1-f][1,2,4]triazin-4(3H)- one - A substrate for the preparation of phosphodiesterase (5) inhibitors
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Imidazo[5,1-f][1,2,4]triazin-4(3H)-ones, as isosteres of purine, are of interest for pharmaceutical research as potential substrates for the synthesis of cGMP-PDE5 inhibitors. We present a novel, alternative method for the synthesis of imidazotriazinones, that differs from the previously reported ones with respect to the method of construction of the triazinone ring in the molecule. The key step in our approach is condensation of an appropriate α-keto-ester with amidrazones, leading to the triazinone heterocycle. Several different substituted imidazolotriazinones have been synthesized in this manner.
- Olszewska, Teresa,Gajewska, Ewa P.,Milewska, Maria J.
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p. 474 - 480
(2013/02/23)
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- Dynamic kinetic asymmetric synthesis of substituted pyrrolidines from racemic cyclopropanes and aldimines: Reaction development and mechanistic insights
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An enantioselective preparation of 2,5-cis-disubstituted pyrrolidines has been achieved via a dynamic kinetic asymmetric transformation (DyKAT) of racemic donor-acceptor cyclopropanes and (E)-aldimines. Mechanistic studies suggest that isomerization of the aldimine or resultant iminium to the Z geometry is not a pathway that furnishes the observed 2,5-cis-disubstituted products.
- Parsons, Andrew T.,Smith, Austin G.,Neel, Andrew J.,Johnson, Jeffrey S.
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supporting information; experimental part
p. 9688 - 9692
(2010/09/06)
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- Triton B-mediated efficient and convenient alkoxylation of activated aryl and heteroaryl halides
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A simple and convenient one-pot synthesis of aryl alkyl ethers by the alkoxylation of aryl halides with alcohol in the presence of Triton B as a base is described. The procedure is applicable for a variety of aryl and heteroaryl halides, and yields are very good. The use of a nonmetallic base and solvent-free conditions are important features of the reaction. Copyright Taylor & Francis Group, LLC.
- Meshram,Goud, P. Ramesh,Reddy, B. Chennakesava,Kumar, D. Aravind
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experimental part
p. 2122 - 2129
(2010/08/13)
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- Novel imidazotriazinones and the use thereof
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Novel imidazotrizinones of general formula (I), a method for the production and the pharmaceutical use thereof are disclosed.
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- Novel imidazo[1,3,5]triazinones and the use thereof
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The invention relates to novel imidazo[1,3,5]triazinones of the general formula (I), to a method for their production and to their use as medicaments, in particular as inhibitors of cyclic GMP metabolising phosphodiesterases.
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- Process for the preparation of sulphonamide-substituted imidazotriazinones
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The present invention relates to a process for the preparation of sulphonamide-substituted imidazotriazinones of the general formula (I) characterized in that compounds of the formula (II) are reacted with sulphuric acid and the products obtained are then reacted with thionyl chloride and converted in situ in an inert solvent using an amine into the compounds according to the invention and, if appropriate, reacted to give the corresponding salts, hydrates or N-oxides.
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- 2-Phenyl-substituited Imidazotriazinones as Phoshodiesterase Inhibitors
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2-(Sulfamoyl-substituted phenyl)-3H-imidazo (5,1-f) (1,2,4) triazin-4-ones (I) are new. Imidazotriazinones of formula (I) and their salts, N-oxides and isomeric forms are new: R1 = H or 1-4C alkyl; R2 = 1-4C straight chain alkyl; R3, R4 = H, 2-8C alkenyl, 1-8C alkoxy or 1-10C alkyl (optionally interrupted by O and/or substituted by a very wide range of specific groups); or R3 or R4 = NR20R21, adamantyl, 2,2-dimethyl-4-phenyl-1,3-dioxan-5-yl, sulfolanyl, hydroxy-sulfolanyl, 2-oxo-tetrahydrofuran-3-yl; or 3-8C cycloalkyl, 6-10C aryl or 5-7 membered heterocycle, all optionally substituted by specific groups; or NR3R4 = (a) optionally benzo-fused, saturated, partially unsaturated or unsaturated 5-7 membered heterocycle, optionally containing 1-3 of S, N, O and NR37 and optionally substituted by a very wide range of specific groups; or (b) a group of formula (i)-(iv); R20,R21 = H or 1-6C alkyl; R37 = H, OH, CHO, CF3, up to 4C acyl, up to 4C alkoxycarbonyl, 1-4C alkoxy, 1-6C alkyl (optionally substituted by specific groups) or -(CO)iE; i = 0 or 1; E = 3-7C cycloalkyl or benzyl; 6-10C aryl or 5- or 6-membered heteroaryl, both optionally substituted by specific groups ; or 5-methyl-1-oxo-2,1,3-oxadiazol-4-yl, N-methylpiperazino or morpholino; R5,R6 = H, 1-6C alkyl, OH or 1-6C alkoxy. The full definitions are given in the DEFINITIONS (Full Definitions) field. An Independent claim is included for the preparation of (I).
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- 2-phenyl substituted imidazotriazinones as phosphodiesterase inhibitors
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The 2-phenyl-substituted imidazotriazinones having short, unbranched alkyl radicals in the 9-position are prepared from the corresponding 2-phenyl-imidazotriazinones by chlorosulphonation and subsequent reaction with the amines. The compounds inhibit cGMP-metabolizing phosphodiesterases and are suitable for use as active compounds in pharmaceuticals, for the treatment of cardiovascular and cerebrovascular disorders and/or disorders of the urogenital system, in particular for the treatment of erectile dysfunction.
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- 7-alkyl- and cycloalkyl-substituted imidazotriazinones
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The present invention relates to 7-alkyl- and cycloalkyl-substituted imidazotriazinones, to processes for their preparation and to their use as medicaments, in particular as inhibitors of cGMP-metabolizing phosphodiesterases.
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- Nickel/zinc-mediated synthesis of aromatic nitriles from aromatic oxime ethers
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Treatment of o-alkoxybenzaldoxime ethers 3 with an equimolar amount of NiCl2 and 3 equimolar amounts of Zn gave o-alkoxybenzonitriles 4 in good yields. It is suggested that the reaction proceed via coordination of the ether oxygen atom of alkyl
- Maeyama, Katsuya,Kobayashi, Masato,Kato, Hiroshi,Yonezawa, Noriyuki
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p. 2519 - 2525
(2007/10/03)
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- Reactions of 1-(2-alkoxyphenyl)alkaniminyl radicals
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Reactions of 1-(2-alkoxyphenyl)alkaniminyl radicals were studied. Generation of the iminyls 1d and 1e by standard methods in the gas-phase by flash vacuum pyrolysis (FVP) gives rise to 1,3-benzoxazines 18 and 22 by a mechanism which probably involves a 1,6-hydrogen atom translocation. The results showed that the dealkylation is an integral part of the reaction mechanism and not a subsequent reaction of 2-alkoxybenzonitriles.
- Leardini, Rino,McNab, Hamish,Minozzi, Matteo,Nanni, Daniele,Reed, David,Wright, Andrew G.
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p. 2704 - 2710
(2007/10/03)
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- A convenient one-step method for converting electron-rich aromatic aldehydes into nitriles
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Electron-rich aromatic aldehydes react with sodium azide in the presence of aluminum chloride in boiling tetrahydrofuran to give the corresponding nitriles in good yields, while electron-deficient or hindered aromatic aldehydes lead to (diazidomethyl) arenes in moderate yield under similar conditions.
- Suzuki,Nakaya
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p. 641 - 642
(2007/10/02)
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