Azatropolones. Part II. The Schmidt Reaction of 2-Methoxy-5-methylbenzoquinone

1974 ◽  
Vol 52 (19) ◽  
pp. 3327-3330 ◽  
Author(s):  
Colin G. Hughes ◽  
Errol G. Lewars ◽  
Alun H. Rees
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Sodium Azide ◽  
Phosphorus Oxychloride ◽  
Schmidt Reaction ◽  
Ring Contraction

2-Methoxy-5-methylbenzoquinone undergoes reaction with sodium azide in sulfuric acid to give (a) 3-hydroxy-6-methyl-1H-azepin-2,5-dione, which undergoes ring contraction with base to give 5-methyl-4-pyridone-2-carboxylic acid; (b) 4-methoxy-7-methyl-1H-azepin-2,5-dione, which reacts with phosphorus oxychloride to give methyl 2-chloro-6-methylpyridine-4-carboxylate, not 2-chloro-4-methoxy-7-methyl-5H-azepin-5-one; (c) 7-methoxy-4-methyl-1H-azepin-2,5-dione. The reactions of these compounds are discussed and the evidence for their structures is presented.

The Schmidt reaction of anthraquinones

1982 ◽  
Vol 60 (5) ◽  
pp. 624-628 ◽  
Author(s):  
Cecily A. Flemming ◽  
Sham S. Gandhi ◽  
Martin S. Gibson ◽  
Edward H. Ruediger
Keyword(s):  
Sulfuric Acid ◽  
Amino Acid ◽  
Methyl Ester ◽  
Benzoic Acid ◽  
Sodium Azide ◽  
Schmidt Reaction ◽  
Direct Treatment ◽  
Hydrolysis Of

Schmidt reaction (sodium azide/sulfuric acid) of 1,5- and of 1,8-dichloroanthraquinones gives, in each case, both of the theoretically possible lactams (2,3,5,6-dibenzoazepin-4,7-diones). Two of the four theoretically possible lactams have been identified from Schmidt reaction of 1- and 2-chloroanthraquinones respectively. Methods used include: (a) preferential hydrolysis of one lactam and identification of the isomeric aminoanthraquinone formed on cyclodehydration of the resulting amino acid; (b) identification of the isomeric aminoanthraquinone(s) formed on direct treatment of a lactam (or mixture of lactams) by sulfuric acid; (c) cleavage by potassium tert-butoxide of the amino acid formed by preferential hydrolysis of one lactam and identification of the resulting benzoic acid as its methyl ester.

Tetrazoloquinolines: Synthesis, Reactions, and Applications

2020 ◽  
Vol 24 (4) ◽  
pp. 439-464 ◽  
Author(s):  
Rizk E. Khidre ◽  
Tahah A. Ameen ◽  
Mounir A. I. Salem
Keyword(s):  
Carboxylic Acid ◽  
Chemical Reactions ◽  
Sodium Azide ◽  
Biological Activities ◽  
Quinoline Derivatives ◽  
Pharmacological Activities ◽  
Synthesis Reactions ◽  
Intramolecular Cyclocondensation

This review summarizes the synthesis, reactions, and biological activities of tetrazolo[1,5-a]quinoline derivatives. These derivatives were synthesized by several methods such as i) from the reaction of 2-chloroquinoline with sodium azide ii) from diazotization 2-hydrazinylquinoline derivatives, and iii) from intramolecular cyclocondensation of 2-azidoarylidenes. Also, the chemical reactions and pharmacological activities of some tetrazoloquinolines such as tetrazolo[1,5-a]quinoline-4-carbaldehyde, 5-chlorotetrazolo[ 1,5-a]quinoline, 4-(chloromethyl)tetrazolo[1,5-a]quinoline, tetrazolo[1,5- a]quinoline-4-carboxylic acid, and 5-azidotetrazolo[1,5-a]quinoline were discussed.

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.

Isocarbostyrils. II. The Conversion of 2-Methyl-4-acyl-5-nitroisocarbostyrils to 2-Substituted Indole-4-carboxylic Acids

1971 ◽  
Vol 49 (17) ◽  
pp. 2797-2802 ◽  
Author(s):  
D. E. Horning ◽  
G. Lacasse ◽  
J. M. Muchowski
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Alkaline Hydrolysis ◽  
Mannich Reaction ◽  
Reductive Cyclization ◽  
Acid Catalyzed ◽  
Acid Anhydrides ◽  
Hydrolysis Of ◽  
Derivatives Of

The sulfuric acid catalyzed acylation of 2-methyl-5-nitroisocarbostyril with carboxylic acid anhydrides gave the corresponding 4-acylated derivatives 3, which underwent reductive cyclization to 2-substituted derivatives of 4-methyl-1,3,4,5-tetrahydropyrrolo[4.3.2.de]isoquinolin-5-one (4). Alkaline hydrolysis of the six-membered lactam in 4 was accompanied by a retro-Mannich reaction to produce 2-substituted indole-4-carboxylic acids in about 40 % overall yield from 3.

Corrosion Inhibition of Copper in Aerated 0.5 M Sulfuric Acid by Indole-2-Carboxylic Acid

CORROSION ◽  
2005 ◽  
Vol 61 (11) ◽  
pp. 1041-1049 ◽  
Author(s):  
G. Quartarone ◽  
A. Zingales ◽  
T. Bellomi ◽  
L. Bonaldo ◽  
M. Gajo ◽  
...  
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Corrosion Inhibition

Hydrogen bonding in cyclic complexes of carboxylic acid–sulfuric acid and their atmospheric implications

RSC Advances ◽  
2016 ◽  
Vol 6 (75) ◽  
pp. 71733-71743 ◽  
Author(s):  
Hailiang Zhao ◽  
Qun Zhang ◽  
Lin Du
Keyword(s):  
Hydrogen Bonding ◽  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Particle Formation ◽  
New Particle Formation ◽  
Ring Structures ◽  
Cyclic Complexes

Carboxylic acids form cyclic ring structures with sulfuric acid and they could potentially be important in new particle formation.

scholarly journals Facile Synthesis of 3-(Azol-1-yl)-1-adamantanecarboxylic Acids—New Bifunctional Angle-Shaped Building Blocks for Coordination Polymers

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2717 ◽  
Author(s):  
Dmitry Pavlov ◽  
Taisiya Sukhikh ◽  
Evgeny Filatov ◽  
Andrei Potapov
Keyword(s):  
Sulfuric Acid ◽  
Carboxylic Acid ◽  
Coordination Polymers ◽  
Building Blocks ◽  
X Ray Diffraction ◽  
Facile Synthesis ◽  
X Ray ◽  
Adamantanecarboxylic Acid ◽  
Concentrated Sulfuric Acid ◽  
First Time

For the first time, orthogonally substituted azole-carboxylate adamantane ligands were synthesized and used for preparation of coordination polymers. The angle-shaped ligands were prepared by the reaction of 1-adamantanecarboxylic acid and azoles (1H-1,2,4-triazole, 3-methyl-1H-1,2,4-triazole, 3,5-dimethyl-1H-1,2,4-triazole, 1H-tetrazole, 5-methyl-1H-tetrazole) in concentrated sulfuric acid. Variation of the solvent and substituents in azole rings allowed to prepare both 1D and 2D copper(II) and nickel(II) coordination polymers, [Cu2(trzadc)4(H2O)0.7]∙DMF∙0.3H2O, [Cu(trzadc)2(MeOH)]∙MeOH, [Ni(trzadc)2(MeOH)2] and [Cu2(mtrzadc)3(MeOH)]+NO3– (trzadc-3-(1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid; mtrzadc-3-(3-methyl-1,2,4-triazol-1-yl)-adamantane-1-carboxylic acid) which were structurally characterized by single crystal X-ray diffraction. Complex [Cu(trzadc)2(MeOH)]∙MeOH was shown to act as a catalyst in the Chan-Evans-Lam arylation reaction.

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