Reduction of 1-Hydroxyimino-1,2,3,4-tetrahydrocarbazoles by Metal and Baker’s Yeast – Syntheses of Aminocarbazole Derivatives

2004 ◽  
Vol 59 (9) ◽  
pp. 1054-1058 ◽  
Author(s):  
Isravel A Danish ◽  
Karnam J. R. Prasad

1-Hydroxyimino-1,2,3,4-tetrahydrocarbazoles (1) were reduced with zinc in acetic acid and acetic anhydride and with bakers’ yeast in an aim to synthesize 1-aminocarbazoles, but interestingly the reaction gave hitherto unknown compounds, 2-acetoxy-1-(acetylamino)carbazoles (2) and 6- [acetoxy(hydroxy)methyl]-1-hydroxylaminocarbazoles (3), respectively. A plausible mechanism for the formation of compounds 2 and 3 is proposed. All new compounds were characterised by IR, NMR, mass spectral methods and elemental analysis.

2004 ◽  
Vol 59 (6) ◽  
pp. 711-715 ◽  
Author(s):  
Isravel A. Danish ◽  
Karnam J. R. Prasad

The reaction of 1-oxo-1,2,3,4-tetrahydrocarbazoles (1) with crotonic acid in polyphosporic acid afforded hitherto unknown 5-methyl-1,2,3,4,5,6-hexahydrocyclopenta[g]carbazole-1,7-diones (2) and 6-crotonyl-2-isopropyl-1-oxo-1,2,3,4-tetrahydrocarbazoles (3) in a single step. A plausible mechanism for the formation of the title compounds has been proposed, and all new compounds were characterized by IR, NMR, mass spectral methods and elemental analysis.


2004 ◽  
Vol 59 (1) ◽  
pp. 106-108 ◽  
Author(s):  
Isravel A. Danish ◽  
Karnam J. R. Prasad

Abstract 2-Benzylidene-1-oxo-1,2,3,4-tetrahydrocarbazoles (1a - e) obtained from the corresponding 1- oxo-1,2,3,4-tetrahydrocarbazoles on reaction with malononitrile in dry benzene with sodium hydride afforded 3-cyano-5,6-dihydro-2-ethoxy-4-phenyl-pyrido[2,3-a]carbazoles (2a - e) in good yields. A plausible mechanism for the formation of the title compound has been proposed and all the compounds were characterised by IR, NMR, mass spectral methods and elemental analysis.


2019 ◽  
Vol 70 (11) ◽  
pp. 3769-3774
Author(s):  
Elena Valentina Rosca ◽  
Theodora Venera Apostol ◽  
Constantin Draghici ◽  
Octavian Tudorel Olaru ◽  
Laura Ileana Socea ◽  
...  

This paper presents the synthesis of new heterocyclic compounds from oxazoles and triazinones classes. Some 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids were condensed with 4-iodobenzaldehyde in presence of acetic anhydride and sodium acetate, when the new corresponding unsaturated oxazol-5(4H)-one were obtained. Through the reaction of these oxazol-5(4H)-ones with phenylhydrazine, in presence of the acetic acid and sodium acetate, the new heterocyclic compounds from 1,2,4-triazin-6(5H)-ones class were obtained. The structures of synthesized compounds have been confirmed by spectral methods (FT-IR, 1H-NMR, 13C-NMR and MS) and elemental analysis. The cytotoxicity of the compounds was evaluated using the Daphnia magna and Artemia salina bioassays.


2019 ◽  
Vol 70 (11) ◽  
pp. 3769-3774
Author(s):  
Elena Valentina Rosca ◽  
Theodora Venera Apostol ◽  
Constantin Draghici ◽  
Octavian Tudorel Olaru ◽  
Laura Ileana Socea ◽  
...  

This paper presents the synthesis of new heterocyclic compounds from oxazoles and triazinones classes. Some 2-(4-(4-X-phenylsulfonyl)benzamido)acetic acids were condensed with 4-iodobenzaldehyde in presence of acetic anhydride and sodium acetate, when the new corresponding unsaturated oxazol-5(4H)-one were obtained. Through the reaction of these oxazol-5(4H)-ones with phenylhydrazine, in presence of the acetic acid and sodium acetate, the new heterocyclic compounds from 1,2,4-triazin-6(5H)-ones class were obtained. The structures of synthesized compounds have been confirmed by spectral methods (FT-IR, 1H-NMR, 13C-NMR and MS) and elemental analysis. The cytotoxicity of the compounds was evaluated using the Daphnia magna and Artemia salina bioassays.


1991 ◽  
Vol 56 (12) ◽  
pp. 2917-2935 ◽  
Author(s):  
Eva Klinotová ◽  
Václav Křeček ◽  
Jiří Klinot ◽  
Miloš Buděšínský ◽  
Jaroslav Podlaha ◽  
...  

3β-Acetoxy-21,22-dioxo-18α,19βH-ursan-28,20β-olide (IIIa) reacts with acetic anhydride in pyridine under very mild conditions affording β-lactone IVa and γ-lactones Va and VIIa as condensation products. On reaction with pyridine, lactones Va and VIIa undergo elimination of acetic acid to give unsaturated lactones VIIIa and IXa, respectively. Similarly, the condensation of 20β,28-epoxy-21,22-dioxo-18α,19βH-ursan-3β-yl acetate (IIIb) with acetic anhydride leads to β-lactone IVb and γ-lactone Vb; the latter on heating with pyridine affords unsaturated lactone VIIIb and 21-methylene-22-ketone Xb. The structure of the obtained compounds was derived using spectral methods, particularly 1H and 13C NMR spectroscopy; structure of lactone IVa was confirmed by X-ray diffraction.


2006 ◽  
Vol 10 (07) ◽  
pp. 996-1002 ◽  
Author(s):  
Ayhan Nazli ◽  
Ergün Gonca ◽  
Ahmet Gül

Magnesium porphyrazinate substituted with eight (1-naphthyl) groups on the peripheral positions has been synthesized by cyclotetramerization of 3,4-(1-naphthyl)pyrroline-2,5-diimine, 4-(1-naphthyl)pyrroline-2,5-diimine in the presence of magnesium butanolate. Its demetalation by treatment with trifluoroacetic acid, resulted in a partially oxidized product, namely, octakis(1-naphthyl)-2-seco-porphyrazine-2,3-dione. Further reaction of this product with copper(II) acetate, zinc(II) acetate and cobalt(II) acetate led to the metallo derivatives, [octakis(1-naphthyl)-2-seco-2,3-dioxoporphyrazinato]M(II) ( M = Cu , Zn or Co ). These new compounds have been characterized by elemental analysis, together with FT-IR, 1 H NMR, UV-vis and mass spectral data.


2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Mohamed Alswah ◽  
Adel Ghiaty ◽  
Ahmed El-Morsy ◽  
Kamal El-Gamal

2-([1,2,4]Triazolo[4,3-a]quinoxalin-4-ylthio)acetic acid hydrazide (10) was used as a precursor for the syntheses of novel quinoxaline derivatives with potential anticonvulsant properties. The newly synthesized compounds have been characterized by IR, 1H NMR, and mass spectral data followed by elemental analysis. The anticonvulsant evaluation was carried out for eleven of the synthesized compounds using metrazol induced convulsions model and phenobarbitone sodium as a standard. Among this set of tested compounds, two of them (14, and 15b) showed the best anticonvulsant activities.


1991 ◽  
Vol 27 (1) ◽  
pp. 55-63 ◽  
Author(s):  
T. H. Aarnio ◽  
M. L. Suihko ◽  
V. S. Kauppinen

2016 ◽  
Vol 9 (1) ◽  
pp. 23-27 ◽  
Author(s):  
Miroslava Puchoňová ◽  
Vladimír Kuchtanin ◽  
Milan Mazúr ◽  
Dušan Valigura

Abstract Four new compounds of formulae [Cu(3-Mesal)2(etbzim)2] (1), [Cu(4-Mesal)2(etbzim)2] (2), [Cu(4-MeOsal)2(etbzim)2] (3), [Cu(5-MeOsal)2(etbzim)2] (4) where 3- or 4-Mesal = 3- or 4-methylsalicylate anionic ligand, 4- or 5-MeOsal = 4- or 5-methoxysalicylate anionic ligand, etbzim = 2-ethylbenzimidazole) have been prepared and characterised by elemental analysis and available spectral methods (EPR, UV-vis and IR spectra). EPR spectra of all measured complexes are axial symmetry. Other spectral methods led to conclusion that all prepared complexes probably contain the etbzim ligand coordinated in equatorial plane together with the asymmetrically bonded salicylato anions thus giving {CuN2O2O’O”} chromophore. The supposed structural motive for all prepared complexes might be simmilar to those benzoate complexes with benzimidazole [Cu(4-OHbz)2(bzim)2] and [Cu(4-Mebz)2(bzim)2] (4-OHbz = 4-hydroxybenzoate, 4-Mebz = = 4-methylbenzoate), but similarity with polymeric salicylate complex [Cu(sal)2(bzim)2]n cannot be excluded.


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