Synthesis of 2-amino-5,7-dimethyl-4-oxopyrido[3,4-e]-1,3-thiazines

1983 ◽  
Vol 48 (12) ◽  
pp. 3426-3432 ◽  
Author(s):  
Dušan Koščík ◽  
Pavol Kristian ◽  
Ondrej Forgáč
Keyword(s):  
Spectral Data ◽  
Chlorine Atom ◽  
Mass Spectra ◽  
High Reactivity ◽  
Secondary Amines ◽  
Dimroth Rearrangement ◽  
H Nmr ◽  
New Synthesis ◽  
C Nmr

New synthesis of pyrido[3,4-e]-1,3-thiazines consisting in reaction of 2,6-dimethyl-4-chloronicotinoyl isothiocyanate with primary or secondary amines, or with benzaldehyde phenylhydrazone, is described. High reactivity of the chlorine atom does not allow isolation of the corresponding thioureas, arising as intermediates, except in the case of the benzylamino derivative. Structure of the products was unequivocally confirmed by their spectral data (IR, UV, 1H NMR, 13C NMR and mass spectra). The synthesized derivatives do not undergo the Dimroth rearrangement.

New synthesis of 2-amino-4-oxopyrido[3,2-e]-1,3-thiazines and 1-alkyl(aryl)pyrido[3,2-e]-2-thiouracils

1983 ◽  
Vol 48 (11) ◽  
pp. 3315-3328 ◽  
Author(s):  
Dušan Koščík ◽  
Pavol Kristian ◽  
Jozef Gonda ◽  
Emília Dandárová
Keyword(s):  
Mass Spectra ◽  
Nmr Spectra ◽  
Secondary Amines ◽  
Primary Amines ◽  
Addition Reactions ◽  
Alkyl Aryl ◽  
H Nmr ◽  
New Synthesis ◽  
Subsequent Cyclization ◽  
C Nmr

Addition reactions of 2-chloronicotinoyl isothiocyanate with primary and secondary amines and subsequent cyclization of intermediate thioureas represent new synthesis of pyrido[3,2-e]thiouracil and pyrido[3,2-e]-thiazine derivatives. 2-Amino-4-oxopyrido[3,2-e]-1,3-thiazines are formed upon heating the reaction components in ethanol, whereas 1-alkyl(aryl)pyrido[3,2-e]-2-thiouracils are products of alkali-catalyzed reaction. In reaction with primary amines the corresponding thioureas were isolated as intermediates, whereas secondary amines reacted directly to give the pyridothiazine derivatives. Structure of the synthesized compounds was confirmed by their 13C NMR and mass spectra; also the IR and 1H NMR spectra are in accord with the suggested formulae.

Synthesis and Pharmacological Evaluation of a Novel Series of Cyclopentenone Derivatives

2017 ◽  
Vol 41 (1) ◽  
pp. 50-56 ◽  
Author(s):  
Fatma A. El-Samahy ◽  
Marwa El-Hussieny ◽  
Naglaa F. El-Sayed ◽  
Elsayed M. Shalaby ◽  
Fayez H. Osman
Keyword(s):  
Mass Spectra ◽  
Secondary Amines ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Chemical Structures ◽  
Pharmacological Evaluation ◽  
New Compounds ◽  
C Nmr ◽  
Boiling Toluene

A novel series of cyclopent-2-enone derivatives have been synthesised by the reaction of 4-hydroxy-3,4-diphenylcyclopent-2-enone, cyclic secondary amines, phosphorus reagents, hexamethylphosphoramide and Lawesson's reagent in boiling toluene/THF. The chemical structures of new compounds were identified by 1H NMR, 13C NMR, 31P NMR and mass spectra. Furthermore, the structure of one of the synthesised compounds has been confirmed using single crystal X-ray diffraction. The pharmacological evaluation results of antilung and anticolon carcinoma cell line properties for the products are discussed.

Reactions and spectral properties of ethyl 5-aminofuroate and its derivatives

1980 ◽  
Vol 45 (1) ◽  
pp. 135-141 ◽  
Author(s):  
Josef Prousek ◽  
Adolf Jurášek ◽  
Jaroslav Kováč
Keyword(s):  
Spectral Data ◽  
Spectral Properties ◽  
Mass Spectra ◽  
Condensation Product ◽  
H Nmr ◽  
Acyl Derivatives ◽  
C Nmr

Ethyl 5-aminofuroate (II), prepared by reduction of ethyl 5-nitrofuroate (I), served for preparation of bifunctional α,β-substituted aminofurans IV-IX, acyl derivatives IIIa, IIIb and condensation product X. The latter reacted with diazomethane directly to afford the corresponding aziridine derivative XI. The synthesized compounds were characterized by spectral data (IR, UV, 1H-NMR, 13C-NMR (XI) and mass spectra.)

Synthesis and properties of 2,5-dimethyl-3-furoylthioureas

1991 ◽  
Vol 56 (8) ◽  
pp. 1711-1718 ◽  
Author(s):  
Adolf Jurášek ◽  
Viktor Badory ◽  
Vladimír Žvak ◽  
Jarmila Štetinová
Keyword(s):  
Spectral Data ◽  
Mass Spectra ◽  
Aliphatic Amines ◽  
H Nmr ◽  
C Nmr

Addition of a series of aromatic or aliphatic amines to 2,5-dimethyl-3-furoyl isothiocyanate (I) afforded the corresponding N-(2,5-dimethyl-3-furoyl)-N’-aryl- or alkylthioureas II or III. Spectral data (IR, UV, 1H NMR, 13C NMR and mass spectra) of compounds prepared are presented.

Oxynemorensine, an alkaloid from Senecio nemorensis L., var. subdecurrens GRISEB

1980 ◽  
Vol 45 (2) ◽  
pp. 548-558 ◽  
Author(s):  
Antonín Klásek ◽  
Petr Sedmera ◽  
Jindřich Vokoun ◽  
Anna Boeva ◽  
Svatava Dvoráčková ◽  
...  
Keyword(s):  
Unsaturated Acid ◽  
Mass Spectra ◽  
H Nmr ◽  
C Nmr

From S. nemorensis L., var. subdecurrens GRISEB. there were isolated the previously obtained alkaloids nemorensine (I), retroisosenine (II), bulgarsenine (III) and, in addition, the alkaloid oxynemorensine which was assigned the structure VIII on the basis of the interpretation of the 1H-NMR, 13C-NMR, mass spectra, and on that of the identification of the products of hydrolysis and reduction. Furthermore, the isolation of the cis-nemorensic acid (V) as well as that of the unsaturated acid IV, and the transformation of bulgarsenine (III) to nemorensine (I) were described.

21,22-Disubstituted 18α,19βH-Ursane Derivatives with Oxabicyclooctane System in Ring E

1993 ◽  
Vol 58 (1) ◽  
pp. 173-190 ◽  
Author(s):  
Eva Klinotová ◽  
Jiří Klinot ◽  
Václav Křeček ◽  
Miloš Buděšínský ◽  
Bohumil Máca
Keyword(s):  
Spectral Data ◽  
Spin Systems ◽  
Coupling Constants ◽  
Complete Analysis ◽  
Nmr Spectrum ◽  
Proton Proton ◽  
H Nmr ◽  
Proton Coupling ◽  
C Nmr

Reaction of 3β-acetoxy-21,22-dioxo-18α,19βH-ursan-28,20β-olide (IIIa) and 20β,28-epoxy-21,22-dioxo-19α,19βH-ursan-3β-yl acetate (IIIb) with diazomethane afforded derivatives XII-XIV with spiroepoxide group in position 21 or 22, which were further converted into hydroxy derivatives XV and XVII. Ethylene ketals VIII-X were also prepared. In connection with the determination of position and configuration of the functional groups at C(21) and C(22), the 1H and 13C NMR spectral data of the prepared compounds are discussed. Complete analysis of two four-spin systems in the 1H NMR spectrum of bisethylenedioxy derivative Xb led to the proton-proton coupling constants from which the structure with two 1,4-dioxane rings condensed with ring E, and their conformation, was derived.

scholarly journals Design and synthesis of a novel 5-(aminomethylene)thiazolidine-2,4-dione derivatives as potent hepatitis-B virus polymerase inhibitors

2015 ◽  
Vol 10 (2) ◽  
pp. 271
Author(s):  
Wei-Guo Li ◽  
He-Qun Wang
Keyword(s):  
Hbv Dna ◽  
Biologically Active ◽  
Secondary Amines ◽  
Design And Synthesis ◽  
H Nmr ◽  
Viral Antigens ◽  
Polymerase Inhibitors ◽  
Potent Inhibition ◽  
B Virus ◽  
C Nmr

<p>A series of novel thiazolidinedione analogues (TZD) were designed and synthesized potent inhibitors of HBV capsid assembly. The synthesis of thiazolidine-2,4-dione derivatives (4a–4o), starting from the condensation of 5-(ethoxymethylene)thiazolidine-2,4-dione (1) with various secondary amines (3) derived from biologically active compounds. The newly synthesized TZD analogues 4a-4o were characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and MS and evaluated for their anti-HBV activity. Most of the compounds inhibited the expression of viral antigens at low concentration. Six compounds, 4g, 4h, 4l, 4m, 4n, and 4o, demonstrated potent inhibition of HBV DNA replication at submicromolar range. Of these five initial hits, compound 4o was the most active when compared with lamivudine.</p><p> </p><p> </p>

Evaluation of Antinociceptive and Anti-Inflammatory Activities of a New Triterpene Saponin from Bauhinia variegata Leaves

2009 ◽  
Vol 64 (11-12) ◽  
pp. 798-808 ◽  
Author(s):  
Mona A. Mohamed ◽  
Madeha R. Mammoud ◽  
Heiko Hayen
Keyword(s):  
High Resolution ◽  
Spectral Data ◽  
Cinnamic Acid ◽  
Cinnamic Acid Derivatives ◽  
Triterpene Saponin ◽  
H Nmr ◽  
Antischistosomal Activity ◽  
Bauhinia Variegata ◽  
Anti Inflammatory ◽  
C Nmr

A new triterpene saponin, named as 23-hydroxy-3α-[O-α-L-1C4-rhamnopyranosyl-(1´´4´)- O-α-L-4C1-arabinopyranosyl-oxy]olean-12-en-28-oic acid O-α-L-1C4-rhamnopyranosyl- (1´´´´´→4´´´´)-O-β-D-4C1-glucopyranosyl-(1´´´´→6´´´)-O-β-D-4C1-glucopyranosyl ester (9), was isolated from the leaves of Bauhinia variegata Linn. In addition, six flavonoid compounds along with two cinnamic acid derivatives were isolated and identified based on their chromatographic properties, and chemical and spectral data (ESI-high resolution-MSn, 1H NMR, 13C NMR, 1H-1H COSY, HSQC, and HMBC). Compound 9 was found to be nontoxic (LD50) and to have significant anti-inflammatory and antinociceptive activities. It also showed a slight antischistosomal activity.

scholarly journals A New Isocoumarin from Cajanus cajan (Fabaceae)

2014 ◽  
Vol 9 (4) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Virginia F. Rodrigues ◽  
Rodrigo R. Oliveira ◽  
Maria Raquel G. Vega
Keyword(s):  
Spectral Data ◽  
Cajanus Cajan ◽  
Mass Spectra ◽  
2D Nmr ◽  
C Nmr

A new isocoumarin, 3-phenyl-8-hydroxy-6-methoxy-5-γ, γ-dimethylallyl-isocoumarin, named cajavilmina (1) and eight known compounds: α-amirenone (2), β-amirenone (3), lupenone (4), 5-hydroxy-7-methoxydihydroflavone (5), longistilin C (6), 3-hydroxy-5-methoxystilbene (7), β-sitosterol (8) and stigmasterol (9) were identified in a dichloromethane fraction from Cajanus cajan leaves. Structures were elucidated by analysis of spectral data, mainly those afforded by 1H, NOEDIFF and 13C NMR (1D and 2D NMR HMQC, HMBC and COSY) and mass spectra.

Synthesis and reactions of substituted benzofuro[3,2-b]pyrrole derivatives

1982 ◽  
Vol 47 (12) ◽  
pp. 3288-3296 ◽  
Author(s):  
Alžbeta Krutošíková ◽  
Jaroslav Kováč ◽  
Miloslava Dandárová ◽  
Mária Bobálová
Keyword(s):  
Electron Impact ◽  
Mass Spectra ◽  
Pyrrole Derivatives ◽  
H Nmr ◽  
Electron Impact Mass ◽  
Impact Mass ◽  
C Nmr

This paper deals with the preparation of ethyl benzofuro[3,2-b]pyrrole-2-carboxylate, its hydrolysis, N-alkylation, and reduction. Also the synthesis of new heterocyclic systems, benzofuro[3,2-b]pyrrole and 2H-dihydrobenzofuro[2',3':4,5]pyrrolo[1,2-d]-1,2,4-triazin-1-one, is described. The structure of 14 new substances was corroborated by IR, UV, 1H NMR, 13C NMR and electron impact mass spectra.

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