cas 699-98-9, 2,3-Pyridinedicarboxylic anhydride

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SYNTHESIS OF A SICKLE CELL DISEASE AGENT AND INTERMEDIATES THEREOF
New processes for preparing 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5- yl)pyridin-3-yl)methoxy)benzaldehyde, an agent developed for the treatment of sickle cell disease, and intermediates thereof, are provided herein.
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Page/Page column 26

(2021/11/13)

Novel synthesis method of 3-fluoropyridine-2-methanol
The invention relates to the field of compound preparation, in particular to a novel synthesis method of 3-fluoropyridine-2-methanol. The 3-fluoropyridine-2-methanol has a structure as shown in a formula V. According to the synthesis method, cheap quinolinic acid is used as an initial raw material, the target product namely 3-fluoropyridine-2-methanol is obtained through the steps of anhydride, esterification, ammoniation, amino fluorination, ester group reduction, and the like, and the structure of the target product is characterized by 1HNMR and 13CNMR. The synthetic method is a brand new synthetic method of 3-fluoropyridine-2-methanol, and has the advantages of low cost, simple technology, high yield, good quality, and high industrialization value.
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Paragraph 0013; 0032-0033

(2020/04/22)

Synthesis method of imazapyracid
The invention relates to a synthesis method of imazapyracid, relates to a preparation method of a compound, and in particular, relates to a production and synthesis method of imazapyracid; the methodis characterized by comprising the steps: taking quinolinic acid as a raw material and reacting with acetic anhydride to generate 2,3-pyridine dicarboxylic anhydride; and under a low-temperature condition, continuously reacting with alcohol to generate a compound represented by a structural formula (I), carrying out a ring closing reaction with 2-amino-2,3-dimethylbutyramide under an alkaline condition, extracting to adjust the pH value, and thus obtaining the imazapyracid product. The method has the advantages that a novel method for obtaining imazapyracid is provided, the route reaction speed is high, the product purity is extremely high, the yield is high, the reaction conditions are mild, isomers are avoided, catalysts are not needed, three wastes are few, the synthesis process is extensive, the reaction conditions are optimized, the reaction equipment cost is reduced, generated products are easy to separate, and the production process is simplified.
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Paragraph 0021; 0024; 0026; 0028; 0030; 0032; 0034; 0036

(2021/01/11)

Design and synthesis of novel PARP-1 inhibitors based on pyridopyridazinone scaffold
Various pyridopyridazinone derivatives were designed as Poly(ADP-ribose) polymerase-1 (PARP-1) inhibitors. The pyridopyridazinone scaffold was used as an isostere of the phthalazine nucleus of the lead compound Olaparib in addition to some modifications in the tail part of the molecule. Preliminary biological evaluation indicated that most compounds possessed inhibitory potencies comparable to Olaparib in nanomolar level. The best PARP-1 inhibitory activity was observed for compound 8a with (IC50 = 36 nM) compared to Olaparib as a reference drug (IC50 = 34 nM). Molecular modeling simulation revealed that, the designed compounds docked well into PARP-1 active site and their complexes are stabilized by three key hydrogen bond interactions with both Gly863 and Ser904 as well as other favorable π-π and hydrogen-π stacking interactions with Tyr907 and Tyr896, respectively. Computational ADME study predicted that the target compounds 8a and 8e have proper pharmacokinetic and drug-likeness properties. These outcomes afford a new structural framework for the design of novel inhibitors for PARP-1.
Elmasry, Ghada F.,Aly, Enayat E.,Awadallah, Fadi M.,El-Moghazy, Samir M.
p. 655 - 666
(2019/04/04)

Preparation method of moxifloxacin important intermediate (by machine translation)
The invention discloses a preparation method, of an important intermediate of moxifloxacin. 2, 3 - Picolinic acid and acetic anhydride are charged first to the reaction kettle, stirred, and stirred to prepare a reaction feed liquid; a first reaction liquid is pumped into a continuous acid removal system filled with an acid remover, and then the reaction liquid is pumped into second reaction kettle; the second reaction kettle is used for stirring reaction; and after the reaction is finished, the reaction mixture liquid is stirred by 2nd. Concentration, a significant intermediate, namely compound 6 - benzyl - 555H-pyrrolo [3, 4 - b] pyridine -5, 7 - (6H) - diketone, is obtained under reduced pressure. The method effectively improves the conversion, greatly improves the yield, enhances the operability, realizes low energy consumption, and can realize the purpose. (by machine translation)
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Paragraph 0029-0032; 0035-0038; 0041-0044; 0047-0050; 0053

(2019/10/01)

Efficient cyclodehydration of dicarboxylic acids with oxalyl chloride
Literature examples illustrating the use of oxalyl chloride to prepare dicarboxylic acid anhydrides are surprisingly limited. At the same time, we have discovered a method involving the use of this readily available reagent which allowed the preparation of novel cyclic anhydrides where other, more conventional, methods had failed. Herein, we demonstrate that the method is applicable to a wide diversity of substrates, delivers good to excellent yields of cyclic anhydrides without chromatographic purification and can be considered a synthetic tool of choice whenever dicarboxylic acid cyclodehydration is required.
Kantin, Grigory,Chupakhin, Evgeny,Dar'in, Dmitry,Krasavin, Mikhail
supporting information
p. 3160 - 3163
(2017/07/18)

Efficient synthesis of (S,S)-2,8-diazabicyclo[4.3.0]nonane
An efficient synthetic route for moxifloxacin chiral intermediate via five steps was established. First, dehydration, N-acylation, and cyclization were combined in one pot to meet the industrial requirement. Then relatively low hydrogen pressure was employed in the catalytic hydrogenation reaction with high yield. Isopropanol/water system was used in resolution, which guaranteed high yield and perfect optical purity. The racemic process conducted by manganese dioxide and Pd/C successfully converted the undesired enantiomer into the racemate and hence the total yield increased remarkably. Furthermore, mild hydrogen transfer catalytic hydrogenation method was utilized in debenzylation process instead of high-pressure hydrogenation. Total yield of 39.0% was achieved, which was much higher than that of 29.0% in literature.
Chen, Shipeng,Liu, Dongqi,Si, Leilei,Chen, Ligong,Yan, Xilong
supporting information
p. 238 - 244
(2017/01/22)

1, 2, 3, 4- [...] compound and process for the synthesis of
The invention provides a synthetic and technological method of a 1,2,3,4-tetrahydrophthalazine compound used as an intermediate of bactericides and anti HIV (human immunodeficiency virus) and other new drugs. The 1,2,3,4-tetrahydrophthalazine compound is obtained by using various cheap and easily accessible phthalic acid or phthalic anhydride as a raw material for two steps of reaction. The method is easily accessible in raw material, low in cost, simple in reaction, easy in control, simple in processing and easy in amplification, and a large number of industrial by-product hydrazide can be found to be directly used as a raw material for the second step. The method is convenient to economic, reuses the industrial by-product as the raw material, and provides a feasible synthetic production and technological method of the 1,2,3,4-tetrahydrophthalazine compound for green chemical industry.
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Paragraph 0029-0032

(2017/03/08)

Design, Synthesis, Antifungal Activities and SARs of (R)-2-Aryl-4,5-dihydrothiazole-4-carboxylic Acid Derivatives
Based on the structure of natural product 2-aryl-4,5-dihydrothiazole-4-carboxylic acid, a series of novel (R)-2-aryl-4,5-dihydrothiazole-4-carboxylic acid derivatives were designed and synthesized. Their structures were characterized by 1H NMR, 13C NMR and HRMS. The single crystal structure of compound 9b was determined by X-ray diffraction analysis. The antifungal activities were evaluated for the first time. The bioassay results indicated that most compounds exhibited moderate to good antifungal activities. The antifungal activities of compound 13a (against Cercospora arachidicola Hori), 13d (against Alternaria solani), and 16e (against Cercospora arachidicola Hori) were 61.9%, 67.3% and 61.9%, respectively, which are higher than those of the commercial fungicides chlorothalonil and carbendazim. Moreover, compound 13d exhibited excellent antifungal activities against 7 kinds of the fungi tested (66.7%, 77.3%, 63.0%, 87.9%, 70.0%, 70.0% and 80.0% at 50 μg?mL). Therefore, 13d can be used as a new lead structure for the development of antifungal agents.
Liu, Jingbo,Li, Yuxin,Chen, Youwei,Hua, Xuewen,Wan, Yingying,Wei, Wei,Song, Haibin,Yu, Shujing,Zhang, Xiao,Li, Zhengming
p. 1269 - 1275
(2015/11/27)

Rilyazine Derivatives and Compositions for The Treatment of Cancer
The present application discloses Rilyazine analogs, methods for their preparation, and the treatment of cancer by the administration of an effective amount of the Rilyazine analogs to a patient in need thereof.
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Paragraph 0099; 0100

(2015/03/16)

The transposing of isomer yields in the methanolyses of N-substituted quinolinimides by triethylamine
The effect of triethylamine in transposing the respective yields of the two isomeric esters ensuing from the methanolysis of N-substituted quinolinimides is described and is rationalized with a mechanism.
Van Es, Theodorus,Staskun, Benjamin,Karuso, Peter
experimental part
p. 53 - 61
(2012/06/04)

Dual fluorescent N-Aryl-2,3-naphthalimides: Applications in ratiometric DNA detection and white organic light-emitting devices
A ten element matrix of 5- and 6-substituted-(2,3)-naphthalimides was prepared for the appropriate placement of substituents necessary to promote dual fluorescence (DF). As prescribed by our balanced seesaw photophysical model this matrix yielded nine new DF dyes out of a possible ten compounds. From this set of nine DF dyes, 4-fluoronaphthalic amide (37) was selected as a probe for ratiometric detection of DNA and demonstration of panchromatic emission.
Nandhikonda, Premchendar,Heagy, Michael D.
supporting information; experimental part
p. 4796 - 4799
(2011/01/03)

IMPROVED PROCESS FOR THE PREPARATION OF (S.S)-2.8-DIAZABICYCLO[4.3.0]NONANE
The present invention is directed to an improved industrially viable, cost effective process for manufacturing (S,S)-2,8-Diazabicyclo[4.3.0]nonane in a substantially pure form and consequent conversion to Moxifloxacin hydrochloride monohydrate.
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Page/Page column 6; 9

(2009/11/29)

Convenient synthesis of 3-(1-carboxyalkyl)pyrido-[2,3-d]pyrimidine-2,4-diones
A cheap and safe synthetic route to obtain 3-(1-carboxyalkyl)pyrido[2,3-d]pyrimidinediones (carboxyalkyl = -CHRCO2H; R = H; CH2; CH2Ph: Ph; CH2 (C3H3N2); (CH2)2CO2H; CH2CO2H) starting from 2,3-pyridinedicarboxylic acid is described. A process scheme consistent with empirical observations is proposed.
Saoud,Benabdelouahab,Guemmout, F. El,Romerosa
p. 306 - 309
(2007/10/03)

Chiral NADH models with restricted or blocked rotation at the amide function: Attempts to interpret the mechanism of the enantioselective hydrogen transfer to methyl benzoylformate
Various NADH models with the following characteristics were studied and compared with previously reported models: (1) use of (S)-phenylalaninol as chiral auxiliary; (2) orientation in or out of the plane of the amide carbonyl. Despite the occurrence of apparently similar characteristics, they gave very different results in the asymmetric reduction of methyl benzoylformate. A detailed NMR study was performed in order to explain the behaviour of these models.
Vitry, Christiane,Bédat, Joelle,Prigent, Yann,Levacher, Vincent,Dupas, Georges,Salliot, Isabelle,Quéguiner, Guy,Bourguignon, Jean
p. 9101 - 9108
(2007/10/03)

Convenient Synthesis of 3-(1-carboxyalkyl)pyrido[2,3-d]pyrimidine-2,4-diones
Cheap and safety synthetic route to obtain 3-(1-carboxyalkyl)pyrido[2.3-d]pyrimidinediones (carboxyalkyl = -CHRCO2H; R = H, 7; CH2 8; CH2Ph, 9; Ph. 10; CH2(C3H3N2, 11; (CH2)2CO2H, 12; CH2CO2H, 13) starting from 2.3-pyridinedicarboxylic acid, 1, is described. A process scheme consistent with empirical observations is proposed.
Saoud,Benabdelouahab,El Guemmout,Romerosa
p. 439 - 444
(2007/10/03)

Stereoselectivity of cyclisations via N-acyliminium ions to form pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine ring systems
Pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine derivatives are obtained by heating in polyphosphoric acid (PPA) appropriate hydroxy lactam precursors derived from pyridine-2,3-dicarboximides. The stereoselectivity of ring closure is rationalised by considering the development of A(1,3) strain in the cyclisation step from N-acyliminium ion intermediates.
Bahajaj,Vernon,Wilson
p. 1446 - 1451
(2007/10/03)

NITROGEN OXIDES OF AZA- AND DIAZA-ANTHRACENEDIONE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS ANTITUMOR AGENTS
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(2008/06/13)

Hetero-annulated indazoles
This invention is directed to heteroannulated indazoles namely to 2,5-disubstituted quinolino-, isoquinolino-, phthalazino-, and quinoxalino- annulated indazole-6(2H)-ones and related mono N-oxides. These compounds have been shown to have antitumor activity.
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(2008/06/13)

The synthesis of 6,9-difluorobenzo[g]quinoline-5,10-dione. Displacements of the fluorides by diamines which lead to 6,9- bis[(aminoalkyl)amino]benzo[g]quinoline-5,10-diones
The synthesis of 6,9-difluorobenzo[g]quinoline-5,10-dione (3b) is described. Facile ipso substitutions of the fluorides from 3b by diamines readily yield the corresponding 6,9-bis[(aminoalkyl)amino]benzo[g]quinoline- 5,10-diones 2. The analogue 2d has been synthesized by side arm modifications of dione 8a.
Krapcho,Petry,Landi Jr.,Stallman,Polsenberg,Hacker,Spinelli,Oliva,Di Domenico,Menta
p. 1565 - 1570
(2007/10/02)

Regioselective Formation of Hydroxy Lactams from Pyridine-2,3-dicarboximides and their Cyclodehydration to Pyridopyrrolo-fused Heterocyclic Systems
Grignard reactions of pyridine-2,3-dicarboximides involve attack at the carbonyl group closer to the pyridine nitrogen atom to give 7-hydroxypyrrolopyridin-5(7H)-one derivatives.Reduction of the same imides with sodium borohydride gives mixtures of regiosomeric hydroxy lactams, in which the 7-hydroxypyrrolopyridin-5-ones are the major components.Hydroxy lactams derived by either of these two methods from pyridine-2,3-dicarboximides containing N-benzyl, N-2-phenylethyl, N-2-(indol-3-yl)ethyl, or N-biphenyl-2-yl substituents are cyclised by heating in trifluoroacetic or polyphosphoric acid to give derivatives of new pyridopyrrolo-fused heterocyclic systems.
Hitchings, Gregory J.,Vernon, John M.
p. 1757 - 1763
(2007/10/02)

Metalated Heterocycles in the Synthesis of Ellipticine Analogues. A New Route to the 10H-Pyridocarbazole Ring System
A synthesis of the 10H-pyridocarbazole ring system is described, in which the key steps are regiospecific acylation of a 2-lithio-1-(phenylsulfonyl)indole (7) with 2,3-pyridinedicarboxylic anhydride (8), cyclization of the deprotected keto acid 10 to keto lactam 11 with acetic anhydride, and the addition of methyllithium to give, after reduction of the diol 12 with sodium borohydride, the target ring system.In this fashion, 5,11-dimethyl-10H-pyridocarbazole (3) and the corresponding 7-methoxy (4) and 8-methoxy (5) derivatives were synthesized.
Gribble, Gordon W.,Fletcher, Gillian L.,Ketcha, Daniel M.,Rajopadhye, Milind
p. 3264 - 3269
(2007/10/02)

Pyridine derivatives and their herbicidal compositions
A pyridine derivative having the formula: STR1 wherein one of A, B, D and E is oxygen, sulfur, --SO--, --SO2 --, --NR3 --, STR2 or =CH-- with the rest being all carbon atoms; X is halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 haloalkyl, C1 -C4 haloalkoxy, C1 -C4 alkylthio, C1 -C4 haloalkylthio, C1 -C4 alkoxycarbonyl, C1 -C4 alkylthioalkyl, tetrahydrothiopyranyl, hydroxyl, CF3, phenyl or pyridyl; n is an integer of from 0 to 6,; W is oxygen or sulfur; R is hydrogen, di-lower alkylimino, C1 -C5 alkyl, C2 -C5 alkenyl, C2 -C5 alkynyl, C4 or C5 oxacycloalkyl, C2 -C5 mono-, di- or tri-haloalkenyl, C2 -C5 haloalkynyl, glycidyl, furfuryl, alkylthioalkyl, C3 -C6 cycloalkyl or a cation R1 is C1 -C4 alkyl, R2 is C1 -C4 alkyl or C3 -C6 cycloalkyl, or R1 and R2 together with the ajacent carbon atom, form C3 -C6 cycloalkyl; and R3 is hydrogen or C1 -C3 alkyl. The compounds are used as herbicides.
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(2008/06/13)

Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids
The invention provides a process for the preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids.
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(2008/06/13)

Benzocyclobutenes. Part 4. Synthesis of Benzocyclobutene-1,2-diones by Pyrolytic Methods
Oxidation of the cyclic hydrazides prepared from phthalic anhydrides in the presence of anthracene gives the corresponding Diels-Alder adducts which, on flash vacuum pyrolysis, give benzocyclobutene-1,2-dione (BBD) and its 4-chloro, 3,6- and 4,5-dichloro, 4,5-dibromo, and 4,5-dimethyl derivatives in 75-98percent yield.Cyclobuta- and cyclobuta-naphthalene-1,2-dione as well as cyclobuta- and cyclobuta-pyridine-1,2-dione have been prepared similarly; the last three of these diones are very unstable.Cyclobutanaphthalene-1,2-dione has also been made by pyrolysis of benzindene-1,2,3-trione.Attempts to make thiophen and furan analogues of BBD from appropriate anthracene adducts failed as did attempts to make tetrachloro- and tetrabromo-derivatives of BBD by the pyrolysis of tetrahalogenophthalimidosulphoximides.
Gould, Ken J.,Hacker, Nigel P.,McOmie, John F. W.,Perry, David H.
p. 1834 - 1840
(2007/10/02)