29096-99-9Relevant academic research and scientific papers
[4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles
Bi, Xihe,Ning, Yongquan,Sivaguru, Paramasivam,Wang, Hongwei,Zanoni, Giuseppe
supporting information, (2021/09/30)
1-Substituted 1,2,3-triazoles represents ‘privileged’ structural scaffolds of many clinical pharmaceuticals. However, the traditional methods for their preparation mainly rely on thermal [3 + 2] cycloaddition of potentially dangerous acetylene and azides. Here we report a base-mediated [4 + 1] annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones (DFHZ-Ts) with amines under relatively mild conditions. This azide- and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner. This transformation has great functional group tolerance and can suit a broad substrate scope. Furthermore, the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality, practicability and applicability.
Synthetic method of allopurinol
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Paragraph 0005; 0026; 0030; 0034; 0038; 0042; 0046; 0050, (2018/03/01)
The invention relates to a synthetic method of allopurinol. The synthetic method comprises the following steps: (1) adding methyl cyanoacetate, triethyl orthoformate and ethyl acetic anhydride into areaction kettle, and stirring and heating for reflux, so as to obtain red brown alpha-ethoxylated methyl cyanoacetate; (2) adding absolute ethyl alcohol and hydrazine hydrate into the reaction kettle,heating for reflux, cooling for crystallization, and filtering, so as to obtain a crystal 3-amino-4-methoxycarbonyl pyrazole; (3) adding 3-amino-4-methoxycarbonyl pyrazole and formamide into the reaction kettle, stirring for reaction, and cooling for crystallization, so as to obtain crude allopurinol; and (4) adding an acid liquid into the reaction kettle, adding crude allopurinol and activated carbon, carrying out suction filtration while the liquid is hot, and carrying out low-temperature crystallization, so as to obtain allopurinol. The method is simple in process, the yield and purity ofthe product are effectively increased, the energy consumption is low in the reaction process, the environmental pollution is low, the raw materials are easily available, the price of allopurinol is low, the quality of the allopurinol is controllable, and an allopurinol finished product meets the standards of 2015 edition of the Pharmacopoeia and is suitable for industrial production.
Production of azo pigment
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Paragraph 0132; 0133; 0134, (2019/06/18)
PROBLEM TO BE SOLVED: To provide a method for manufacturing an azo pigment, which can manufacture the azo pigment having a specific chemical structure in a high efficiency; and to provide an azo pigment manufactured by the same. SOLUTION: The azo pigment represented by formula (2) is manufactured using an acid salt of an amine represented by formula (1). In the formula (2), R1and R2are each independently a hydrogen atom or a substituent. COPYRIGHT: (C)2012,JPOandINPIT
Pyrazolopyrimidines
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Page/Page column 46, (2008/12/09)
Pyrazolopyrimidines of the formula in which R1, R2, R3, R4, R5 and X are as defined in the description, processes for preparing these compounds and their use for controlling unwanted microorganisms.
ALPHA-UNSUBSTITUTED ARYLMETHYL PIPERAZINE PYRAZOLO[1,5-A] PYRIMIDINE AMIDE DERIVATIVES
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Page/Page column 167-168, (2008/12/08)
Methods of preventing, treating or delaying the onset of HIV in a subject by administering to the subject novel pharmaceutically active arylmethyl pyrazolo[1,5-α ]pyrimidine amide derivatives, or pharmaceutical compositions containing the same are described. Additionally, compounds of novel pharmaceutically active arylmethyl piperazine pyrazolo[l,5-α]pyrimidine amide derivatives and their use for the manufacture of specific medicaments are described.
QUINAZOLINE DERIVATIVES
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Page/Page column 44, (2010/02/11)
The invention relates to the use of compounds of the formula I: wherein: ring C is a 5-6 membered heterocyclic moiety; Z is -O-, -S-, or -CH2-; R1 is hydrogen, C1-4alkyl, C1-4alkoxymethyl, di(C1-4)alkoxy)methyl, C1-4alkanoyl, trifluoromethyl, cyano, amino, C2-5alkenyl, C2-5alkynyl, carboxy, C3-7cycloalkyl, C3-7-cycloalkylC1-3alkyl, or an optionally substituted group selected from phenyl, benzyl, phenylC2-4alkyl and a 5-6 membered heterocyclic group; n is an integer from 0 to 5; m is an integer from 0 to 3; R2 represents hydrogen, hydroxy, halgeno, cyano, nitro, trifluoromethyl, C1-3alkyl, C1-3alkoxy, C1-3alkylsulphanyl, -NR3R4 (wherein R3 and R4, which may be the same or different, each represents hydrogen or C1-3alkyl), or R5X1- (wherein X1 represents a direct bond, -CH2-, or a heteroatom linker group and R5 is an alkyl, alkenyl or alkynyl chain optionally substituted by for example hydroxy, amino, nitro, alkyl, cycloalkyl, alkoxyalkyl, or an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, which alkyl, alkenyl or alkynyl chain may have a heteroatom linker group, or R5 is an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, and salts thereof, in the manufacture of a medicament for use in the production of an antiangiogenic and/or vascular permeability reducing effect in warm-blooded animals, processes for the preparation of such compounds, pharmaceutical compositions containing a compound of formula I or a pharmaceutically acceptable salt thereof as active ingredient and compounds of formula I. The compounds of formula I and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.
Substituted anilino-quinazoline (or quinoline) compounds and use thereof
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, (2008/06/13)
The invention concerns amide derivatives of Formula (I), wherein: G is N or CH; R1is a group such as hydroxy, halo, trifluoromethyl, C1-6alkyl and C1-6alkoxy; each of R2and R3is hydrogen, halo, C1-6alkyl, C2-6alkenyl or C2-6alkynyl; R4is a group such as hydrogen, hydroxy, C1-6alkyl, C1-6alkoxy and C3-7cycloalkyl, or R4is of the Formula (IC): —K—J, wherein J is aryl, heteroaryl or heterocyclyl and K is a bond or a group such as oxy and imino, R5is a group such as hydrogen, halo and trifluoromethyl: m is 1-3 and q is 0-4; or pharmaceutically acceptable salts or in vivo cleavable esters thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical conditions mediated by cytokines.
Cyanoacrylate Inhibitors of the Hill Reaction I. Nature of the Inhibitor/Receptor Site Interaction
Phillips, John N.,Huppatz, John L.
, p. 51 - 54 (2007/10/02)
A series of alkyl 3-alkylamino-2-cyanoacrylates was synthesized and assayed as inhibitors of the Hill reaction in isolated pea chloroplasts.The results suggest that there is a single centre in these molecules, possibly the carbonyl group, which specifically interacts with the inhibitor receptor site and that maximum activity is associated with an asymmetric distribution about this centre of lipophilic alkyl groups which are involved in non-specific binding to discrete hydrophobic regions.
NUCLEOPHILIC ADDITION OF HYDROXYMETHYL-1,2,3-TRIAZOLES TO MULTIPLE BOND
Tikhonova, L. G.,Maksikova, A. V.,Serebryakova, E. S.,Kaufman, I. G.,Vereshchagin, L. I.
, p. 1104 - 1107 (2007/10/02)
The addition of C- and N-hydroxymethyl-1,2,3-triazoles to the activated multiple bonds of acrylonitrile and benzoylacetone was studied.The structures of the compounds obtained were proved by means of the PMR and IR spectra.
Cyanoacrylates. Herbicidial and Photosynthetic Inhibitory Activity
Huppatz, John L.,Phillips, John N.,Rattigan, Barbara M.
, p. 2769 - 2774 (2007/10/02)
Various alkyl 3-ohenylamino-2-cyano- and 2-ethoxycarbonylacrylates and 3-phenylamino-2-cyanoacrylonitriles were synthesized and assayed as inhibitors of the Hill reaction in isolated pea chloroplast suspensions and as pre- and post-emergent herbicides on mustard and barnyard grass.Many of the compounds were potent Hill reaction inhibitors and several showed significant herbicidial activity.
