51 research outputs found
An efficient improved one-pot synthesis of thiazolo<span style="mso-ansi-language:SV;mso-bidi-font-weight: bold" lang="SV">[2,3-<i style="mso-bidi-font-style:normal">c</i>][1,2,4]triazol-5-yl)-2<i style="mso-bidi-font-style:normal">H</i>-chromen-2-one derivatives <i style="mso-bidi-font-style:normal">via</i> multi-component approach </span>
115-119An efficient
improved protocol has been developed for the synthesis of various
thiazolo-triazoles via a
three-component reaction of various 3-(2-bromoacetyl)-2<i style="mso-bidi-font-style:
normal">H-chromen-2-one, thiosemicarbazide and aromatic/aliphatic
carboxylic acids using phosphorous
oxychloride as the cyclizing agent in toluene at reflux. This method is simple, efficient and
requires shorter reaction times in comparison to the multi-step synthesis. The
structures of the newly synthesized compounds have been established from
analytical and spectral data.
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Synthesis of substituted 3-(3-(4-hydroxy- 6-methyl-2-oxo-2<i style="mso-bidi-font-style:normal">H</i>-pyran-3-yl)imidazo- [2,1-<i style="mso-bidi-font-style:normal">b</i>]thiazol-6-yl)-2<i style="mso-bidi-font-style:normal">H</i>-chromen-2-ones and <span style="mso-bidi-font-weight:bold">substituted 4-hydroxy-6-methyl-3- (6-phenylimidazo[2,1-<i style="mso-bidi-font-style:normal">b</i>]thiazol-3-yl)- 2<i style="mso-bidi-font-style:normal">H</i>-pyran-2-one derivatives </span>
811-814An easy, highly efficient and a
new convenient two-step approach to the synthesis of
3-(3-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)imidazo[2,1-<i style="mso-bidi-font-style:
normal">b]thiazol-6-yl)-2H-chromen-2-one
derivatives and 4-hydroxy-6-methyl-3-(6-phenylimidazo[2,1-<i style="mso-bidi-font-style:
normal">b]thiazol-3-yl)-2H-pyran-2-one
derivatives is described. These compounds have been synthesized from 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, thiourea, various
3-(2-bromoacetyl)-2H-chromen-2-ones
and phenacyl bromides in good yields. The structures of newly prepared
compounds have been confirmed by their analytical and spectral data.</i
One-pot synthesis of coumarin substituted dihydrofurans
1417-1420A sequential one-pot
two-step tandem reaction for an efficient synthesis of 2,3-dihydrofurans
substituted with 2H-benzopyrans has
been developed. One-pot reaction of in
situ formed benzopyran substituted pyridinium ylides with aromatic
aldehydes and dimedone gives corresponding 2,3-dihydrofurans in good yields. The
structures of the final compounds have been assigned as <i style="mso-bidi-font-style:
normal">trans-2,3-dihydrofurans on the basis of their NMR spectra
Novel one-pot expeditious synthesis of 2,4-disubstituted thiazoles through a three-component reaction under solvent free conditions
<p>An expeditious one pot method has been developed for the synthesis of 2,4-disubstituted thiazoles under solvent free conditions via a multicomponent approach. Substituted thiazoles were synthesized with high yields by the reaction of cyclic ketones, thiosemicarbazide, and phenacyl bromides or 3-(2-bromoacetyl)-2<i>H</i>-chromen-2-ones in a shorter reaction time with high purity via simple purification technique.</p
One pot multicoponent synthesis of 4-hydroxy-6-methyl-3-(3-phenylthiazolo [2,3<em>c</em>][1,2,4]triazol-5-yl)-2<em>H</em>-pyran-2-ones
1089-1093An efficient one pot multicomponent reaction for the synthesis of 4-hydroxy-6-methyl-3-(3-phenylthiazolo[2,3-c][1,2,4]triazol-5-yl)-2H-pyran-2-ones with good to excellent yields has been described. Reaction of 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one (1), thiosemicarbazide (2) and various aromatic carboxylic acids (3a-j) in dry toluene and POCl3 affords 4-hydroxy-6-methyl-3-(3-phenylthiazolo[2,3-c][1,2,4]triazol-5-yl)-2H-pyran-2-ones. All the synthesized compounds have been characterized by their analytical and spectral data
A facile one-pot expeditious synthesis of triazolothiadiazines and anticancer activity
A novel, one-pot, multicomponent synthesis of triazolothiadiazine derivatives have been achieved starting from 4-amino-4H-1,2,4-triazole-3,5-dithiol and variously substituted phenacyl bromides. The synthesis involves the simultaneous formation of two C–S and one C = N bond. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectral data. The advantages of this method are good yields, high purity, shorter reaction times and simple purification technique. The synthesized target compounds were screened for their in vitro anticancer activity at concentration 10−5 M against 60 cancer cell lines. Among all the compounds, 1-(4-Fluorophenyl)-2-((6-(4-fluorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl) thio)ethanone (4d), 1-(4-Bromophenyl)-2-((6-(4-bromophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)thio) ethanone (4f), and 2-((6-(4-Chlorophenyl)-7H-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazin-3-yl)thio)-1-(4-fluorophenyl)ethanone (4l) exhibited significant activity in terms of growth percent against renal cancer OU-31 cell line with 47.42%, 46.76%, 48.14%. The compound 2-((6-(4-Chlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)thio)-1-(4-fluorophenyl) ethanone (4l) also exhibited significant activity on leukemia MOLT-4 cell line with 49.82%.</p
One pot multicoponent synthesis of 4-hydroxy-6-methyl-3-(3 phenylthiazolo [2,3<em>c</em>][1,2,4]triazol-5-yl)-2<em>H</em>-pyran-2-ones
960-964An efficient one pot multicomponent reaction for the synthesis of 4-hydroxy-6-methyl-3-(3-phenylthiazolo[2,3-c][1,2,4]triazol-5-yl)-2H-pyran-2-ones with good to excellent yields have been described. Reaction of 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one 1, thiosemicarbazide 2 and various aromatic carboxylic acids 3a-j in dry toluene and POCl3 afford 4-hydroxy-6-methyl-3-(3-phenylthiazolo[2,3-c][1,2,4]triazol-5-yl)-2H-pyran-2-ones. All the synthesized compounds have been characterized from their analytical and spectral data
Synthesis of 2-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-carbonyl)-6,6-dimethyl-3-phenyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one Derivatives via Multicomponent Reaction
<div><p></p><p>A sequential one-pot, two-step reaction for an efficient preparation of 2-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-carbonyl)-6,6-dimethyl-3-phenyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one derivatives has been described. One-pot reaction of in situ–formed benzopyran-substituted pyridinium ylides with aromatic aldehydes and dimedone gives corresponding 2,3-dihydrofurans in good yields. The structures of all the newly synthesized compounds were confirmed from their analytical and spectral data.</p>
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Novel One-Pot Multicomponent Synthesis of Substituted 2,3-Dihydro-2-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)phthalazine-1,4-diones and Substituted 3-[3-(N′-Benzylidene-hydrazino)-7H-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-4-hydroxy-6-methyl-pyran-2-ones
<div><p></p><p>A one-pot procedure has been developed for the synthesis of substituted 2,3-dihydro-2-(6-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7H-[1,2,4]triazolo[3,4-b] [1,3,4]thiadiazin-3-yl)phthalazine-1,4-diones by reaction of 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and phthalic anhydrides in acetic acid medium. Similarly, a one-pot, three-component synthetic procedure has been developed for substituted 3-[3-(N<sup>1</sup>-benzylidene-hydrazino)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-6-yl]-4-hydroxy-6-methyl-pyran-2-ones from 3-(2-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and various aromatic aldehydes in absolute ethanol and a few drops of glacial acetic acid.</p>
<p>[Supplementary materials are available for this article. Go to the publisher's online edition of <i>Synthetic Communications</i>® for the following free supplemental resource(s): Full experimental and spectral details.]</p>
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