Naphthyridines, Pyridoquinolines, Anthyridines and Similar Compounds

Löwe, Pawel

doi:10.1016/b978-008096519-2.00033-3

Cited by 19 publications

(10 citation statements)

References 271 publications

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“…The elemental analysis further corroborated with the molecular formula C17H12N2. All the above spectral and analytical data supported the structure of 3a as 6-methyl dibenzo [b,f ] [1,6] naphthyridines.This reaction sequence leading to 3b-f was confirmed by their spectral data . (Table Π) A facile approach to dibenzo [b,fj [1,6]naphthyridines using Vilsmeier conditions …”

Section: Resultssupporting

confidence: 64%

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A Facile approach to dibenzo [bf| [1,6] naphthyridines using Vilsmeier Conditions

Suresh¹,

Kumar²,

Mohan³

2003

Heterocyclic Communications

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Section: Resultssupporting

confidence: 64%

“…1 " 5 Some recent investigation indicated that 1,6-naphthyridines posses human cytogatovirus inhibitors. 6 ' 7 As number of heterocycles have been synthesized using Vilsmeier reagent,'" 12 we have adapted for same approach to prepare 6-methyl dibenzo[i,/] [1,6] naphthyridines. The reaction route is shown in Scheme I.…”

Section: Introductionmentioning

confidence: 99%

A Facile approach to dibenzo [bf| [1,6] naphthyridines using Vilsmeier Conditions

Suresh¹,

Kumar²,

Mohan³

2003

Heterocyclic Communications

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“…The few complete sets of spectral data found in literature [4,5] were also used in the computation of the tabulated increments. Chemical shift calculations based on suggested formulas can be performed with good accuracy.…”

Section: Resultsmentioning

confidence: 99%

Spectral Characteristics of 2,7-Naphthyridines

2000

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“…Conversely, in tautomeric imino forms of The amino group in 3-aminopyridine, as is known [32], is largely similar in properties to that in aniline. This explains the unambiguous behavior of 3-aminopyridine in reactions with various acylating agents (including imidazolide 2), which results in formation of exocyclic-N-acyl substituted products [33,34], for example amide 5. In the case of 2-and 4-aminopyridines prone to prototropic tautomerism the pattern is quite different.…”

Section: Chemistrymentioning

confidence: 87%

Synthesis and Regularities of the Structure–Activity Relationship in a Series of N-Pyridyl-4-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides

et al. 2019

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According to our quantum and chemical calculations 4-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylic acid imidazolide is theoretically almost as reactive as its 2-carbonyl analog, and it forms the corresponding N-pyridyl-4-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides with many aminopyridines. However, in practice, the sulfo group introduces significant changes at times and prevents the acylation of sterically hindered amines. One of these products was 2-amino-6-methylpyridine. Thus, it has been concluded that aminopyridines interact with imidazolide in aromatic form where the target for the initial electrophilic attack is the ring nitrogen. To confirm the structure of all substances synthesized, 1H-NMR spectroscopy and X-ray diffraction analysis were used. From X-ray diffraction data it follows that in the crystalline phase the carbonyl and sulfo group may occupy different positions with respect to the plane of the benzothiazine bicycle: this position may be unilateral, typical for 4-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides, versatile, and not yet encountered in compounds of this type. A comparison of these data with the results of the pharmacological screening conducted on the standard model of carrageenan inflammation showed that the N-pyridylamides of the first group demonstrated a direct dependence of their analgesic and anti-inflammatory activity on the mutual arrangement of the planes of the benzothiazine and pyridine fragments. The new molecular conformation of the benzothiazine nucleus provides a sufficiently high level of analgesic (but not anti-inflammatory) properties in all N-pyridylamides of the second group with an extremely weak dependence on the spatial arrangement of the pyridine cycle. All substances presented this article proved themselves in varying degrees as analgesics and antiphlogistics. Moreover, two of them—N-(5-methylpyridin-2-yl)- and N-(pyridin-3-yl)-4-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides—exceeded the most effective drug of oxicam type Lornoxicam by these indicators.

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Naphthyridines, Pyridoquinolines, Anthyridines and Similar Compounds

Cited by 19 publications

References 271 publications

A Facile approach to dibenzo [bf| [1,6] naphthyridines using Vilsmeier Conditions

A Facile approach to dibenzo [bf| [1,6] naphthyridines using Vilsmeier Conditions

Spectral Characteristics of 2,7-Naphthyridines

Synthesis and Regularities of the Structure–Activity Relationship in a Series of N-Pyridyl-4-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxamides

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