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 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 Preparation of 2-N-Alkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones and 3,4-Dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine

1993 ◽  
Vol 58 (4) ◽  
pp. 893-901 ◽  
Author(s):  
Dušan Koščík ◽  
Milan Dzurilla ◽  
Peter Kutschy
Keyword(s):  
Mass Spectroscopy ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Alkyl Aryl ◽  
New Approach ◽  
H Nmr ◽  
Primary And Secondary Amines ◽  
Sole Product ◽  
C Nmr

Addition-cyclization reactions of 3-bromo- and 3-chloro-2-methylpropenoylisothiocyanates with primary and secondary amines and alcohols have been studied. The formed addition products, thioureas, underwent cyclization of heating with ethanolic KOH or in dimethylformamide in the presence of lithium hydride. This method represents a new approach to 2-dialkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones. Addition reactions with alcohols afforded 3,4-dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine as the sole product. The structure of the synthesized compounds was confirmed by 1H NMR, 13C NMR, IR and mass spectroscopy.

scholarly journals Metallkomplexe mit Tetrapyrrol-Liganden, XXXVIII [1]. Zur Kenntnis der Alkyl- und Arylimidovanadium(IV)-Porphyrine / Metal Complexes with Tetrapyrrole Ligands, XXXVIII [1]. On the Knowledge of Alkyl- and Arylimidovanadium(IV) Porphyrins

1985 ◽  
Vol 40 (10) ◽  
pp. 1362-1370 ◽  
Author(s):  
Johann W. Buchler ◽  
Stefan Pfeifer
Keyword(s):  
Mass Spectra ◽  
Nmr Spectra ◽  
Primary Amines ◽  
Reactive Intermediate ◽  
H Nmr ◽  
Vanadyl Complex ◽  
Elemental Analyses ◽  
Paramagnetic Metal ◽  
Paramagnetic Complexes ◽  
Proton Resonances

A series of novel alkyl or aryiimidovanadium(IV) 5,10,15,20-tetra(p-tolyl)porphyrinates, VNR(TTP) (4a-4g), is described. They are obtained from the vanadyl complex, VO(TTP) (2a) via the reactive intermediate VCl2(TTP) (3b) which undergoes aminolysis with the respective primary amines RNH2 (R = tBu, Ph, pTol, pClPh, pAnis, pBiph, ptBuPh)**. The formulae are proved by elemental analyses and mass spectra. The paramagnetic complexes are stable to water and may thus be purified by chromatography but are hydrolyzed to give 2 a on treatment with acetic acid. The UV/VIS and 1H NMR spectra of 4a-4g are of the same type as 2a, but the former are slightly hypsochromically shifted, and the latter do not show the proton resonances of the organylimide ligands due to the proximity of the paramagnetic metal center.

Synthesis and investigation of enamine-imine tautomerism of 2,6-disubstituted 4H-1,3-thiazin-4-ones

1982 ◽  
Vol 47 (12) ◽  
pp. 3268-3282 ◽  
Author(s):  
Ján Imrich ◽  
Pavol Kristian
Keyword(s):  
Aromatic Amines ◽  
Mass Spectra ◽  
Secondary Amines ◽  
Alkyl Aryl ◽  
Sodium Hydrosulfide ◽  
H Nmr ◽  
Electron Impact Mass ◽  
Aliphatic Thiols ◽  
Model Substances ◽  
Impact Mass

Substituted thioureas, obtained by reaction of 3-chloro-3-phenylpropenoyl isothiocyanate with primary aliphatic or aromatic amines, were cyclized to 2-N-alkyl(aryl)amino-6-phenyl-4H-1,3-thiazin-4-ones. The enamine-imine tautomerism was investigated by means of infrared and ultraviolet spectra and also by model substances prepared either by reacting the starting isothiocyanate with secondary amines, or by methylation of 2-N-alkyl(aryl)amino-6-phenyl-4H-1,3-thiazin-4-ones. The structure of the synthesized compounds was corroborated by 1H NMR and electron impact mass spectra. 2-N-Arylamino derivatives dissolved in chloroform exist prevalently an imino form whereas 2-N-alkylamino derivatives is an amino form. Reaction of 3-chloro-3-phenylpropenoyl isothiocyanate with aliphatic thiols gave 2-alkylthio-6-phenyl-4H-1,3-thiazin-4-ones and with sodium hydrosulfide (hydroselenide) 6-phenyl-2-thioxo-2,3-dihydro-4H-1,3-thiazin(selenazin)-4-ones.

Anhydrobetulin and its derivatives

1991 ◽  
Vol 56 (4) ◽  
pp. 886-904 ◽  
Author(s):  
Alois Vystrčil ◽  
Václav Křeček ◽  
Jiří Protiva ◽  
Miloš Buděšínský
Keyword(s):  
Double Bond ◽  
Alkaline Medium ◽  
Sodium Borohydride ◽  
Mass Spectra ◽  
Nmr Spectra ◽  
Cotton Effect ◽  
Addition Reactions ◽  
Chemical Transformations ◽  
C Nmr ◽  
Reduction Of Ketones

The structure of anhydrobetulin II and its derivatives I, III and IV has been solved using 1H and 13C NMR spectra, mass spectra and chemical transformations. It has been proven that in addition reactions the trisubstituted double bond is attacked selectively from the α-side under formation of D/E cis-annelated derivatives VIII, X and XI. The 22-oxo derivative XIII exhibits an anomalous Cotton effect and, in contrast to its saturated analogue XXVII,it is not epimerized in alkaline medium. Trinordiketone XXI easily epimerizes to a mixture in which the 17βH-epimer XXIb predominates, trinorketone XXIV is stable only if the annelation of rings D and E is trans. These differences are explained in terms of steric interactions of substituents in position 19. The steric course of reduction of ketones XIII and XXIV with sodium borohydride is described.

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.

Preparation of C(18)-empiric 20,29,30-trinorlupane derivatives. 1H, 13C NMR and mass spectra

1986 ◽  
Vol 51 (3) ◽  
pp. 621-635 ◽  
Author(s):  
Václav Křeček ◽  
Jiří Protiva ◽  
Miloš Buděšínský ◽  
Eva Klinotová ◽  
Alois Vystrčil
Keyword(s):  
Nitrous Acid ◽  
Mass Spectra ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Allylic Oxidation ◽  
Hydroxyl Group ◽  
Methyl Groups ◽  
Unsaturated Ketone ◽  
H Nmr ◽  
C Nmr

Reaction of amide I with nitrous acid gave the olefins II, III and IV. On allylic oxidation of olefin IV α,β-unsaturated ketone V is formed from which olefins VIII and IX were prepared by a sequence of further reactions. Addition of hydrogen to the double bond of olefin IV and α,β-unsaturated ketone V takes place on catalytic hydrogenation from the β-side and leads to derivatives with cis-annellated rings D/E. This made the preparation of hydrocarbons VI and VII epimeric on C(18) possible, which represent reference compounds for the study of the effect of substituents on the chemical shifts of the methyl groups and the saturated carbon atoms of 18αH and 18βH-lupane derivatives. The configuration of the hydroxyl group in epimers XI and XII were derived from 1H NMR spectra. Deuteration of olefins III, IV and IX gave deuteriohydrocarbons XVI to XVIII. The 1H, 13C NMR and mass spectra of the substances prepared are discussed.

scholarly journals Synthesis, Characterization and Antibacterial Activity of Schiff Bases and their Metal Complexes Derived from 4-Acyl-1-phenyl-3-methyl-2-pyrazolin-5-ones and 2-Amino-4(4'-methylphenyl)-thiazole

2010 ◽  
Vol 7 (4) ◽  
pp. 1396-1406 ◽  
Author(s):  
A. S. Thakar ◽  
K. K. Singh ◽  
K. T. Joshi ◽  
A. M. Pancholi ◽  
K. S. Pandya
Keyword(s):  
Antibacterial Activity ◽  
Schiff Bases ◽  
Elemental Analysis ◽  
Mass Spectra ◽  
Nmr Spectra ◽  
Electrical Conductance ◽  
H Nmr ◽  
Infrared Spectral ◽  
Ft Ir ◽  
C Nmr

4-Acyl-1-phenyl-3-methyl-2-pyrazolin-5-ones condensed with 2-amino-4(4'-methylphenyl)-thiazole to form Schiff base. These Schiff bases from complexes of type ML22H2O (M=Mn, Fe, Co, Ni and Cu). Elemental analysis, magnetic susceptibility, electrical conductance, electronic and Infrared spectral data suggested octahedral structure for the complexes. All the compounds were tested for their antibacterial activity. The result indicates that the growth of the tested organism was inhibited by most of the compounds. These Schiff bases are characterized by elemental analysis, mass spectra,1H-NMR spectra,13C NMR spectra and FT IR spectra.

New investigations of the reaction of epichlorohydrin with hindered amines: X-ray and NMR analyses

1989 ◽  
Vol 67 (10) ◽  
pp. 1514-1522 ◽  
Author(s):  
Michel Laguerre ◽  
Chantal Boyer ◽  
Jean-Michel Leger ◽  
Alain Carpy
Keyword(s):  
Hydroxy Group ◽  
Amino Alcohol ◽  
Structure Elucidation ◽  
Nmr Spectra ◽  
Secondary Amines ◽  
Primary Amines ◽  
Nmr Studies ◽  
X Ray ◽  
Hindered Amines ◽  
C Nmr

During the synthesis of a series of new antiarhythmic drugs, the reaction between epichlorohydrin and hindered amines was reinvestigated. With primary amines, 3-azetidinols were formed in fair yields. The X-ray structure elucidation of one of these compounds (1: P21/n, a = 17.210, b = 6.665, c = 23.585, β = 102.29, and R = 0.064 for 2005 observed reflections) and NMR studies led to the conclusion that both the hydroxy group and the bulky nitrogen substituent are on the same side of the azetidine ring. With secondary amines, the reaction was very complex, leading to diamino dioxane, diamino alcohols, amino alcohol ethers, and one glycol. X-ray analysis and 1H and 13C NMR studies allowed complete assignments for all compounds. All but one exhibited a slow interconversion of the nitrogen visible in the 13C NMR spectra. Keywords: epichlorohydrin, hindered amines, azetidinol, adamantane, alkanol amines.

Mikrobielle Produkte, I NMR-Spektren von Nocardamin und Massenspektrum des Tri-O-methyl-nocardamins / Microbiological Products, I NMR Spectra of Nocardamine and Mass Spectra of Tri-O-methyl-nocardamine

1977 ◽  
Vol 32 (8) ◽  
pp. 937-942 ◽  
Author(s):  
Hubert Maehr ◽  
Wolfgang Benz ◽  
Joanne Smallheer ◽  
Thomas H. Williams
Keyword(s):  
Mass Spectra ◽  
Nmr Spectra ◽  
Silver Oxide ◽  
Electron Impact Mass Spectrometry ◽  
Streptomyces Species ◽  
H Nmr ◽  
Fragmentation Mechanisms ◽  
Electron Impact Mass ◽  
Impact Mass ◽  
C Nmr

Nocardamine was isolated from an unidentified Streptomyces, species X-14568, and its 1H NMR and 13C NMR spectra are assigned in detail. Reaction with iodomethane and silver oxide converts nocardamine to the tri-O-methyl ether which is a suitable derivative for electron-impact mass spectrometry. Fragmentation mechanisms of tri-O-methylnocardamine are discussed.

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