619-17-0Relevant articles and documents
Synthesis method of 2,4-diaminobenzoic acid
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, (2016/11/09)
The present invention discloses a synthesis method of 2,4-diaminobenzoic acid, and belongs to the field of chemical synthesis. The synthesis method comprises the following steps: using phthalic anhydride as a raw material; adding concentrated sulfuric acid and fuming nitric acid to generate 4-nitrophthalic acid; adding acetic anhydride into the 4-nitrophthalic acid and heating until the solid is completely dissolved; washing ether to obtain 4-nitro phthalic anhydride; mixing and heating the 4-nitro phthalic anhydride with urea; evacuating a reaction system; then adding hydrochloric acid to obtain 4-nitro-2-formyl acetaminobenzoic acid; obtaining 2-amino-4-nitrobenzoic acid under the conditions of a sodium hypochlorite solution and an ice bath; and finally refluxing with absolute ethanol, and adding an ammonium sulfide solution to finally produce 2,4-diaminobenzoic acid by using microwave heating and other conditions.
Functionalization of quinazolin-4-ones part 1: Synthesis of novel 7-substituted-2-thioxo quinazolin-4-ones from 4-substituted-2-aminobenzoic acids and PPh3(SCN)2
Heppell, Jacob,Al-Rawi, Jasim
, p. 162 - 174 (2014/02/14)
4-(Nitro, amino, acetylamino)-2-aminobenzoic acid were allowed to react with PPh3(SCN)2 and gave the crossholding 7-nitro, 7-acetylamino- and 7-amino-2-thioxo quinazolin-4-ones respectively. The nature of the substituent at position 4 of the 2-aminobenzoic acids has significant influence on the outcome of the cyclisation reaction with PPh 3(SCN)2. Similarly, the nature of the substituent at position 7 of the 2-substituted quinazolin-4-ones significantly affected the ease with which alkylation reactions could be performed. The alkylation selectivity of the 7- substiuted-2-thioxo quinazolin-4-ones was found to depend on the nature of the alkyl halide and the nature of the substituent at position 2.
The detection of glycine from the treatment of glyoxylic acid with iron(II) sulfate and ammonia in water
Plater, M. John,Vassiliev, Ken
experimental part, p. 129 - 132 (2011/07/29)
A glycine/(NH4)2SO4 mixture was isolated by treatment of glyoxylic acid with FeSO4 and aqNH3 in H2O. The yields of glycine were estimated by 1H NMR. Pyruvic acid was not reduced to alanine under these conditions. This method for forming glycine might have occurred prebiotically alongside the Urey-Miller arc discharge method for making amino acids because glyoxylic acid is formed by arc discharge through a N2/CO2 atmosphere and both NH3 and Fe(II) occurred in the earth's early oceans. The carboxylic acid directs the reduction of 2,4-dinitrobenzoic acid to give 2-amino-4-nitrobenzoic acid.
Copper-catalyzed direct amination of ortho-functionalized haloarenes with sodium azide as the amino source
Zhao, Haibo,Fu, Hua,Qiao, Renzhong
experimental part, p. 3311 - 3316 (2010/08/05)
A simple copper-catalyzed direct amination of ortho-functionalized haloarenes (2-halobenzoic acid, 2-halobenzamide, and N-(2-bromophenyl)acetamide derivatives) has been developed with use of NaN3 as the amino source in ethanol, and the corresponding ortho-functionalized aromatic amines were synthesized in good to excellent yields. The protocol undergoes one-pot Ullmann-type coupling of ortho-functionalized haloarenes with NaN3 to lead to ortho-functionalized azidoarenes, followed by reduction with ethanol.
Regio- and chemoselective enzymatic N-oxygenation in vivo, in vitro, and in flow
Winkler, Robert,Richter, Martin E. A.,Knuepfer, Uwe,Merten, Dirk,Hertweck, Christian
, p. 8016 - 8018 (2007/10/03)
(Chemical Equation Presented) Action by the para: Evaluation of the nitro-group-forming N-oxygenase AurF in vivo, in vitro, and immobilized as a fusion protein with simply H2O2 as oxidant (peroxide shunt) reveals para-regioselective oxygenation of aromatic amines (see scheme). This effect includes the selective oxygenation of diamino compounds.
Thermal Stability Studies on a Homologous Series of Nitroarenes
Oxley, Jimmie C.,Smith, James L.,Ye, Hong,McKenney, Robert L.,Bolduc, Paul R.
, p. 9593 - 9602 (2007/10/02)
The thermal stabilities of a number of nitroarenes were examined in solution and in condensed phase.In general, increasing the number of nitro groups decreased thermal stability.Changing the substituent on 1-X-2,4,6-trinitrobenzene from X = H to NH2 to CH3 to OH accelerated decomposition; this effect was attributed to increased ease of intramolecular proton transfer to an ortho nitro group, thus weakening the carbon-nitrogen bond.In solution, the effect of increasing substitution from n = 1 to n = 3 on Xn(NO2)3C6H3-n was uniformly that of decreasing the thermal stability of the species.However, in condensed phase, results suggested that crystal habit may be more important than molecular structure; for X = Br, CH3, and NH2, the more substituted species was the more stable.
DESIGN OF ANTINEOPLASTIC AGENTS ON THE BASIS OF THE "2-PHENYLNAPHTHALENE-TYPE" STRUCTURAL PATTERN.I. SYHTHESIS OF SUBSTITUTED 3-PHENYLQUINAZOLONES, BENZOXAZOLOQUINAZOLONES AND BENZOTHIAZOLOQUINAZOLONES
Cheng, Chia-Chung,Liu, Den-Fu,Chou, Ting-Chao
, p. 775 - 789 (2007/10/02)
A number of substituted 3-phenylquinazolin-4-ones, 12H-benzoxazoloquinazolin-12-ones and 12H-benzothiazoloquinazolin-12-ones were designed and synthesized on the basis of a "2-phenylnaphthalene-type" structural pattern hypothesis.The posulated pattern, which was uncovered among a substantial number of compounds of both natural and synthetic origins, was noted to be associated with compounds possessing a variety of biological properties which include the antineoplastic activity.Several compounds designed for the present study were found to exhibit potentcytotoxicity against the growth of human promyelocytic leukemia (HL-60)cells.
Role of Intermolecular Reactions in Thermolysis of Aromatic Nitro Compounds in Supercritical Aromatic Solvents
Minier, Leanna M.,Brower, Kay R.,Oxley, Jimmie C.
, p. 3306 - 3314 (2007/10/02)
Several nitroarenes were decomposed isothermally in dilute supercritical solution in benzene or toluene and in the vapor phase in the temperature range of 290-380 deg C in sealed glass tubes with pressure up to 100 MPa.The mechanisms of thermolysis are inferred from kinetic studies and product analysis.The initial rate-controlling step for nitrobenzene and p-nitrotoluene decomposition is probably intermolecular hydrogen abstraction to form an ArNO2H radical intermediate.The nature of the transition state is deduced from the activation volume (ΔV*), H/D kinetic-isotope effect, and a linear free-energy relationship between the ionization potential of the hydrogen donor and the logarithm of the decomposition rate.A concurrent pathway for o-nitrotoluene is an intramolecular reaction in which anthranil is an intermediate.The behavior of 1,3-dinitrobenzene and 1,4-dinitrobenzene resembles that of nitrobenzene, whereas 2,4-dinitrotoluene and 2,6-dinitrotoluene decompose in the same manner as o-nitrotoluene.Activation parameters are given and detailed mechanisms proposed.
Anthranilic acid derivatives
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, (2008/06/13)
Agents for lowering glucose levels in blood having the formula: STR1 wherein Ro is bromo, chloro, fluoro, nitro or trifluoromethyl, R is hydrogen, C1-6 alkyl or C2-18 alkanoyl, and R1 is hydrogen or C1-12 alkyl, and the non-toxic, pharmaceutically acceptable salts thereof.
