Attempts at the synthesis of 11-methoxysubstituted benzo[c]phenantridines

1985 ◽  
Vol 50 (4) ◽  
pp. 861-868 ◽  
Author(s):  
Jan Šmidrkal ◽  
Jiří Holubek ◽  
Jiří Šlanger ◽  
Jan Trojánek
Keyword(s):  
Carboxylic Acid ◽  
Methoxyl Group ◽  
Carboxyl Group ◽  
Nitrobenzoic Acid ◽  
Multistep Synthesis

Experiments aimed at the synthesis of so far unknown 11-methoxybenzo[c]phenanthridines (IIa,b,c) are described. In the first approach 2,3,7,8-tetramethoxybenzo[c]phenanthridine-11-carboxylic acid (IIIb) was synthesized using a procedure for the preparation of 2,3,7,8-bis-methylenedioxybenzo[c]phenanthridine-11-carboxylic acid (IIIa). Attempts to convert the carboxyl group of these acids to the methoxyl group were not successful. In the second approach 3-methoxy-6,7-methylenedioxy-l-methylaminonaphthalene (XX) was prepared from l-(3,4-rnethylenedioxyphenyl)-2-propanone (IX) by a multistep synthesis. On acylation of the product with 2,3-dimethoxy-6-nitrobenzoic acid and subsequent hydrogenation N-(3-rnethoxy-6,7-methylenedioxynaphth-l-yl)-N-methylamide of 6-amino-2,3-dimethoxybenzoic acid (XXII) was obtained. The attempts at its cyclization according to Pschorr were unsuccessful.

The inner salt 4-carboxy-2-(pyridinium-4-yl)-1H-imidazole-5-carboxylate monohydrate

2006 ◽  
Vol 62 (7) ◽  
pp. o2751-o2752 ◽  
Author(s):  
Ting Sun ◽  
Jian-Ping Ma ◽  
Ru-Qi Huang ◽  
Yu-Bin Dong
Keyword(s):  
Carboxylic Acid ◽  
Dihedral Angle ◽  
Title Compound ◽  
Acid Group ◽  
Planar Structure ◽  
Carboxyl Group ◽  
Carboxylic Acid Group ◽  
Pyridyl Group ◽  
Compound C

In the title compound, C10H7N3O4·H2O, one carboxyl group is deprotonated and the pyridyl group is protonated. The inner salt molecule has a planar structure, apart from the carboxylic acid group, which is tilted from the imidazole plane by a small dihedral angle of 7.3 (3)°.

Improved synthesis of anti-sesquinorbornene

1984 ◽  
Vol 62 (9) ◽  
pp. 1840-1844 ◽  
Author(s):  
Karl R. Kopecky ◽  
Alan J. Miller
Keyword(s):  
Acetic Acid ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Lead Tetraacetate ◽  
Carboxyl Group ◽  
Silver Acetate ◽  
Benzenesulfonyl Chloride ◽  
Methoxide Ion ◽  
Hydrolysis Of ◽  
Monomethyl Ester

Treatment of methyl hydrogen decahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a,8a-dicarboxylate with lead tetraacetate in benzene – acetic acid replaces the carboxyl group by an acetoxy group. Hydrolysis of this product with 25% sulfuric acid at 130 °C forms 8a-hydroxydecahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a-carboxylic acid 10. The reaction between 10 and benzenesulfonyl chloride in pyridine containing triethylamine at 95 °C produces anti-sesquinorbornene 1 in 34% yield. In the absence of triethylamine 1 is converted to the hydrochloride. The iodohydroperoxide of 1 is converted by silver acetate at 0 °C to the diketone in a luminescent reaction. The 1,2-dioxetane could not be isolated. Decahydro-1,4:5,8-exo,exo-dimethanonaphthalene-4a,8a-dicarboxylic anhydride is converted slowly by methoxide ion in methanol at 150 °C to the monomethyl ester which then undergoes demethylation. The isomeric exo,endo anhydride undergoes reaction readily with methoxide ion at 80 °C.

Azoverdin -an Isopyoverdin

1996 ◽  
Vol 51 (11-12) ◽  
pp. 772-780 ◽  
Author(s):  
R Michalke ◽  
K Taraz ◽  
H Budzikiewiez
Keyword(s):  
Carboxylic Acid ◽  
Succinic Acid ◽  
Peptide Chain ◽  
Side Chain ◽  
Carboxyl Group ◽  
Amino Group ◽  
Present Evidence ◽  
N Terminus

For azoverdin, the siderophore of Azomonas macrocytogenes ATCC 12334, a pyoverdintype structure has been suggested. We now present evidence that it is actually an isopyoverdin. Also the sequence of the peptide chain has to be revised. Azoverdin comprises, therefore, the chromophore (3S)-5-amino-1,2-dihydro-8,9-dihydroxy-3H -pyrimido[1,2a]quinoline- 3-carboxylic acid whose amino group is bound to a succinamide residue while the carboxyl group is attached to the N -terminus of L-Hse-[2-(R-1-amino-3-hydroxypropyl)-3,4,5,6- tetrahydropyrimidine-65-carboxylic acid]-N5-acetyl-N5,-hydroxy-ᴅ-Orn-ᴅ-Ser-N5-acetyl-N5- hydroxy-ʟ-Orn. In addition to azoverdin congeners with succinic acid (azoverdin A ) and with ʟ-Glu (azoverdin G ), resp., instead of the succinamide side chain could be isolated.

The Crystal Structure of Acifluorfen {5-[2-Chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoic Acid}

1987 ◽  
Vol 40 (6) ◽  
pp. 1131 ◽  
Author(s):  
CHL Kennard ◽  
G Smith ◽  
T Hari
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Phenyl Ring ◽  
Acid Group ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
Carboxylic Acid Group ◽  
X Ray ◽  
Nitrobenzoic Acid ◽  
Cell Dimensions

The crystal structure of the herbicide acifluorfen (5-[(2-chloro-4-trifluoromethyl)]phenoxy-2- nitrobenzoic acid] has been determined by X-ray diffraction and refined to a residual of 0.051for 1124 observed reflections. Crystals are monoclinic, space group C2/c with cell dimensions a 26.848(7), b 8 .O29(2), c 19 .Ol4(6) �, ,R l34.72(2)� and Z 8. The molecules form centrosymmetric hydrogen-bonded cyclic dimers [O---0, 2.637(7) �] with the carboxylic acid group and the phenoxy group synclinally related to the first phenyl ring while the nitro substituent isessentially coplanar with the ring.

Synthesis of amino acid diazoketones

1986 ◽  
Vol 64 (11) ◽  
pp. 2097-2102 ◽  
Author(s):  
George R. Pettit ◽  
Paul S. Nelson
Keyword(s):  
Amino Acid ◽  
Carboxylic Acid ◽  
Acid Chloride ◽  
Low Temperatures ◽  
Oxalyl Chloride ◽  
Acyl Chloride ◽  
Carboxyl Group ◽  
Carboxylic Acid Chloride ◽  
Active Esters ◽  
Active Ester

A study of carboxylic acid → diazoketone conversion was pursued employing the γ-carboxyl group of otherwise protected L-glutamic acids. The Arndt–Eistert route employing carboxylic acid chloride intermediates was found best (52% yield, 5b), performed at very low temperatures employing oxalyl chloride in dimethylformamide–tetrahydrofuran followed by diazomethane at −23 °C. Alternatively, substitution of a mixed carbonic anhydride for the acyl chloride led to very similar yields (57% of 5b) of diazoketones (5). Among a series of active ester intermediates (7) examined, only the ODnp (7d) and SPfp (7f) esters were found to react (23–26% yield), at least partially, with diazomethane. The latter two reactions appear to represent the first such examples employing active esters.

scholarly journals 4-Bromobenzoic acid–6-(4-bromophenyl)-3-methyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole (1/1)

2012 ◽  
Vol 68 (4) ◽  
pp. o1185-o1186
Author(s):  
Kamini Kapoor ◽  
Vivek K. Gupta ◽  
Satya Paul ◽  
Seema Sahi ◽  
Rajni Kant
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Maximum Deviation ◽  
Carboxyl Group ◽  
Stacking Interactions ◽  
Acid Molecule ◽  
Ring Plane ◽  
Title 1 ◽  
Benzene Ring Plane

In the title 1:1 co-crystal, C10H7BrN4S·C7H5BrO2, the triazolothiadiazole system is approximately planar [with a maximum deviation of 0.030 (4) Å] and forms a dihedral angle of 8.6 (1)° with the bromophenyl ring. In the carboxylic acid molecule, the carboxyl group is rotated by 6.4 (3)° out of the benzene ring plane. The crystal structure features O—H...N and C—H...O hydrogen bonds, π–π stacking interactions [centroid–centroid distances = 3.713 (2), 3.670 (2) and 3.859 (3) Å] and short S...N [2.883 (4) Å] contacts.

Elimination of carboxyl group in 3,8-dinitro-6-oxo-6H-dibenzo[b,d]pyran-10-carboxylic acid by the action of DMSO or DMFA

1984 ◽  
Vol 20 (12) ◽  
pp. 1396-1396 ◽  
Author(s):  
A. M. Andrievskii ◽  
E. N. Sidorenko ◽  
A. N. Poplavskil ◽  
K. M. Dyumaev
Keyword(s):  
Carboxylic Acid ◽  
Carboxyl Group

scholarly journals Febuxostat ethanol monosolvate

2020 ◽  
Vol 76 (6) ◽  
pp. 816-819
Author(s):  
Thomas Gelbrich ◽  
Volker Kahlenberg ◽  
Verena Adamer ◽  
Sven Nerdinger ◽  
Ulrich J. Griesser
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Title Compound ◽  
Chain Structure ◽  
Hydroxyl Group ◽  
Carboxyl Group ◽  
Hydrogen Bond Donor ◽  
Ethanol Molecule ◽  
Hydrogen Bonded

The title compound, 2-(3-cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic acid ethanol monosolvate, C16H16N2O3S·C2H6O, (I), displays intermolecular O—H...O and O—H...N bonds in which the carboxyl group of the febuxostat molecule and the hydroxyl group of the ethanol molecule serve as hydrogen-bond donor sites. These interactions result in a helical hydrogen-bonded chain structure. The title structure is isostructural with a previously reported methanol analogue.

THE SYNTHESIS OF POSSIBLE DEGRADATION PRODUCTS OF METATHEBAINONE. I.

1944 ◽  
Vol 22b (3) ◽  
pp. 56-65 ◽  
Author(s):  
H. L. Holmes ◽  
L. W. Trevoy
Keyword(s):  
Carboxylic Acid ◽  
Ethyl Ester ◽  
Degradation Products ◽  
Aldehyde Group ◽  
Carboxyl Group ◽  
Unsuccessful Attempt ◽  
Naphthoic Acid ◽  
Relationship Of ◽  
The Relationship ◽  
General Method

The method of Crowley and Robinson (5) for the synthesis of 6-methoxy-3,4-dihydro-2-naphthoic acid has been modified to provide an improved and general method for the synthesis of 3,4-dihydro-2-naphthoic acids. The 7-methoxy-3,4-dihydro-2-naphthoic acid and its ethyl ester have been shown to react with butadiene and 2,3-dimethylbutadiene to give 3-methoxy-5,8,9,10,13,14-hexahydrophenanthrene-14-carboxylic acid and its 6,7-dimethyl derivative. The relationship of these hydrophenanthrenes to possible degradation products of morphine and metathebainone has been discussed. An unsuccessful attempt was made to lengthen the C14-chain by converting the carboxyl group to an aldehyde group by the Rosenmund method followed by condensation with malonic acid. The projected conversion failed in the first stage.

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