Synthesis of isothiocyanates from non-aromatic nitrogen-containing heterocycles

1986 ◽  
Vol 51 (1) ◽  
pp. 112-117 ◽  
Author(s):  
Jozef Gonda ◽  
Pavol Kristian ◽  
Ľubomír Mikler
Keyword(s):  
Spectral Methods ◽  
Mass Spectral ◽  
H Nmr ◽  
C Nmr

Investigation of the reaction of thiophosgene with Δ2-oxazolines I, Δ3-thiazolines II, 4H-benzo[d][1,3]thiazines III, 2-methoxypentahydro-Δ1-azepine IV, theophylline and caffeine showed that only compounds I and IV reacted to give 2-acyloxyethyl isothiocyanates and methyl 6-isothiocyanatohexanoate. The structure of these products was corroborated by IR, 1H NMR, 13C NMR and mass spectral methods. The suitability of the above-mentioned compounds to react is discussed.

Synthetic Utility of 2-Benzylidene-1,2,3,4-tetrahydrocarbazol-1-ones. A Facile Syntheses of Pyrano[2,3-a]carbazoles, Pyrido[2,3-a]carbazoles and Pyridazino[3,4-a]carbazoles

2005 ◽  
Vol 70 (2) ◽  
pp. 223-236 ◽  
Author(s):  
Isravel Antony Danish ◽  
Karnam Jayarampillai Rajendra Prasad
Keyword(s):  
Elemental Analysis ◽  
Spectral Methods ◽  
Mass Spectral ◽  
H Nmr ◽  
Synthetic Utility ◽  
C Nmr

2-Benzylidene-1,2,3,4-tetrahydrocarbazol-1-ones 1, synthons easily accessible from the corresponding 1,2,3,4-tetrahydrocarbazol-1-ones, were utilized in the synthesis of fused carbazoles. In accordance, the reaction of 1 with malononitrile yielded pyrano[2,3-a]carbazoles 2a and 2d or pyrido[2,3-a]carbazoles 2b, 2c and 2e. The reaction of 1 with thiocarbohydrazide or thiosemicarbazide under basic conditions afforded pyridazino[3,4-a]carbazoles 3 or thiol substituted pyridazino[3,4-a]carbazoles 4, respectively, in good yields. The formation of the hitherto unknown compounds was well supported by plausible mechanisms. The products formed were characterized by IR, 1H NMR, 13C NMR, mass spectral methods and by elemental analysis.

Triazolopyridine nucleosides. II. Glycosylations of 3-oxo-s-triazolo[4,3-a]pyridines with accompanying conversions into 2-oxo-s-triazolo[1,5-a]pyridine nucleosides

1977 ◽  
Vol 55 (5) ◽  
pp. 831-840 ◽  
Author(s):  
Brian Maurice Lynch ◽  
Suresh Chandra Sharma
Keyword(s):  
General Structure ◽  
Spectroscopic Properties ◽  
Mass Spectral Fragmentation ◽  
Mass Spectral ◽  
H Nmr ◽  
Pyridine Nitrogen ◽  
Methyl Derivatives ◽  
Fragmentation Patterns ◽  
Ribose Moiety ◽  
C Nmr

3-Oxo-s-triazolo[4,3-a]pyridine and various C-methyl derivatives (general structure 1) have been converted into the 2-β-D-ribofuranosyl species 2 and thence 4 via Friedel–Crafts catalyzed reaction with tetra-O-acetyl-β-D-ribofuranose, followed by deblocking. During the course of these reactions, rearrangements into the isomeric 3-β-D-ribofuranosyl-2-oxo-s-triazolo[1,5-a]-pyridines occur through ring-opening of the pyridine rings yielding species 3 and 5. The proportion of rearrangement products is dependent upon the position and number of the C-methyl substituents.Structural assignments for these compounds are based upon comparisons of spectroscopic properties (1H nmr, 13C nmr, uv) with model compounds from each isomeric series; structural assignments for these models are based on unequivocal mass-spectral fragmentation patterns. Unlike related triazolopyridine nucleosides with the ribose moiety attached to a pyridine nitrogen (Lynch and Sharma (1976)), there are no unusual aspects in the conformations of the nueleosides of types 4 and 5.

Synthesis and Pharmacological Activities of Some New 2-[1-Heptyl-3-(4- methoxybenzyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]acetohydrazide Derivatives

2014 ◽  
Vol 69 (9-10) ◽  
pp. 969-981 ◽  
Author(s):  
Olcay Bekircan ◽  
Emre Mentese ◽  
Serdar Ulker
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Lipase Activity ◽  
Spectral Studies ◽  
Antituberculosis Activity ◽  
Pharmacological Activities ◽  
Mass Spectral ◽  
H Nmr ◽  
Acetohydrazide Derivative ◽  
C Nmr

Abstract In the present investigation, the key intermediate acetohydrazide derivative 5 was synthesized starting from 3-(4-methoxybenzyl)-4-amino-4,5-dihydro-1,2,4-triazol-5-one (1) by a four-step reaction. Thiosemicarbazides 6a-f and arylidenehydrazide derivatives 8a-d were obtained from compound 5. The cyclization of compounds 6a-f in the presence of NaOH resulted in the formation of compounds 7a-f. The compounds were characterized by IR, 1H NMR, 13C NMR spectroscopy, elemental analysis and mass spectral studies. The compounds were tested for their anti-lipase, anti-α-glucosidase and anti-mycobacterial activities. Compounds 6b and 8c exhibited excellent anti-lipase activity, and compound 8d showed excellent anti-a-glucosidase activity. Compounds 3 and 4 exhibited good antituberculosis activity

Synthesis and characterization of N-glucosylated dithiadiazepine derivatives through carbon-sulfur bond formation

2015 ◽  
Vol 21 (5) ◽  
pp. 269-272 ◽  
Author(s):  
Snehal A. Chavan ◽  
Avinash G. Ulhe ◽  
Baliram N. Berad
Keyword(s):  
Bond Formation ◽  
Synthesis And Characterization ◽  
Mass Spectral ◽  
H Nmr ◽  
Chemical Structures ◽  
Elemental Analyses ◽  
New Compounds ◽  
Sulfur Bond ◽  
C Nmr

AbstractNew 4,7-bis(arylamino)-2-tetra-O-acetyl-β-d-glucopyranosylimino-1,3,5,6-dithiadiazepines were synthesized via reaction of N-tetra-O-acetyl-β-d-glucopyranosyl isocyanodichloride with 1,6-diaryl-2,5-dithio-bis-ureas without using any catalyst. Thus, the synthesis of 7-membered heterocycles containing two sulfur and two nitrogen atoms through carbon-sulfur bond formation was explored. The chemical structures of these new compounds were elucidated by IR, 1H NMR, 13C NMR, mass spectral, and elemental analyses.

scholarly journals Synthesis, Antioxidant, Antimicrobial, Antimycobacterial, and Cytotoxic Activities of Azetidinone and Thiazolidinone Moieties Linked to Indole Nucleus

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
A. R. Saundane ◽  
Prabhaker Walmik
Keyword(s):  
Spectral Studies ◽  
Cytotoxic Activities ◽  
Mass Spectral ◽  
H Nmr ◽  
Excellent Activity ◽  
C Nmr

2-N-(2-Phenyl-1H-indol-3-yl)imino-4-arylthiazoles (3a–c) were used as key synthons for the preparation of (4-arylthiazol-2-yl)-4-(2-phenyl-1H-indol-3-yl)azetidin-2-ones (4a–c) and 3-(4-arylthiazol-2-yl)-2-(2-phenyl-1H-indol-3-yl)thiazolidin-4-ones (5a–c). These newly synthesized compounds have been characterized with the help of IR,1H NMR,13C NMR, and mass spectral studies. All compounds were screened for their antioxidant, antimicrobial, antimycobacterial, and cytotoxic activities. Some of the compounds displayed excellent activity.

scholarly journals Approach for the Synthesis of Potent Antimicrobials Containing Pyrazole, Pyrimidine and Morpholine Analogues

2016 ◽  
Vol 69 ◽  
pp. 87-96 ◽  
Author(s):  
Nisheeth C. Desai ◽  
Bonny Y. Patel ◽  
Bharti P. Dave
Keyword(s):  
Antimicrobial Activity ◽  
Dilution Method ◽  
Mass Spectral ◽  
H Nmr ◽  
Sar Studies ◽  
Mueller Hinton ◽  
Morpholine Derivatives ◽  
Mueller Hinton Broth ◽  
C Nmr

The present study is in the interest of some synthesized novel derivatives containing 4-(1,3-diphenyl-1H-pyrazol-4-yl)-N-(morpholinomethyl)-6-arylpyrimidin-2-amines pooled with different bio-active heterocycles such as pyrazole, pyrimidine and morpholine derivatives. The structures of newly synthesized compounds were elucidated by IR, 1H NMR, 13C NMR and mass spectral data. The synthesized compounds were evaluated for their in vitro antimicrobial activity against different bacterial and fungal strains using Mueller-Hinton Broth dilution method. On the basis of SAR studies, it was observed that the presence of electron withdrawing groups remarkably enhanced the antimicrobial activity of synthesized compounds.

scholarly journals Synthesis of New Bicyclic Hydroxamic Acids with Cytotoxic Activity

2018 ◽  
Vol 61 (4) ◽  
Author(s):  
Iker S. Escalona-Torres ◽  
Francisco Yuste ◽  
Rubén Sánchez-Obregón
Keyword(s):  
Cytotoxic Activity ◽  
Nitro Group ◽  
Cell Lines ◽  
Cancer Cell ◽  
Cancer Cell Lines ◽  
Hydroxamic Acids ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
H Nmr ◽  
C Nmr

Six new bicyclic hydroxamic acids were synthesized through an uncommon nitro group rearrangement between β-nitrostyrenes and dimedone. The structures of all the new synthesized compounds were confirmed using a combination of FTIR, <sup>1</sup>H NMR, <sup>13</sup>C NMR and mass spectral data. Likewise, the cytotoxic activity of the obtained products was evaluated in six different cancer cell lines. Two compounds showed significant potency on two cancer cell lines with IC50 between 9.31±0.1 and 23.38±0.9 μM.

scholarly journals Tyrosinase enzyme mediated: Synthesis and larvicidal activity of 1,5-diphenyl pent-4-en-1-one derivatives against Culex quinquefasciatus and investigation of Ichthyotoxicity against O. mossambicus

2021 ◽  
Author(s):  
SathishKumar Chidambaram ◽  
Daoud Ali ◽  
Saud Alarifi ◽  
Surendra Kumar Radhakrishnan ◽  
Idhayadhulla Akbar
Keyword(s):  
Larvicidal Activity ◽  
Culex Quinquefasciatus ◽  
Oreochromis Mossambicus ◽  
Docking Studies ◽  
Reaction Conditions ◽  
Mass Spectral ◽  
H Nmr ◽  
Tyrosinase Enzyme ◽  
High Yields ◽  
C Nmr

Abstract Larvicidal activity of 1,5-diphenylpent-4-en-1-one derivatives were synthesized via grindstone method, tyrosinase enzyme used as a catalyst of this process. This method offers high yields with mild reaction conditions. Synthesized compounds were conformed from FTIR, 1H NMR, 13C NMR, mass spectral and elemental analysis. In this study, a total of 17 compounds (1a–1q) were synthesized, and their larvicidal and antifeedant activities were evaluated. Compound 1i (1-(5-oxo-1,5-diphenylpent-1-en-3-yl)-3-(3-phenylallylidene)thiourea) was extremely active (LD50: 12.09 µg/mL) against Culex quinquefasciatus compared with temephos and permethrin, whereas compounds 1i at 100 µg/mL generated 0% mortality within 24h against Oreochromis mossambicus in an antifeedant screening, and Ichthyotoxicity was determined as the death ratio (%) at 24 h. The compounds 1a, 1e, 1f, 1j, and 1k were found to be highly toxic whereas the 1i was not toxic in antifeedant screening. Therefore, 1i was found to have a high larvicidal activity against C. quinquefasciatus, and was non-toxic to non-target aquatic species. Molecular docking studies also supported the finding that 1i is a potent larvicide with more binding energy than the control (-10.0 vs. -7.6 Kcal/mol) in the 3OGN protein. The lead molecule is very important to larvicidal properties and insecticides.

scholarly journals A Novel and Efficient Synthesis of [1,2,3]-Triazolyl Substituted Benzo[c]Coumarins and Evaluation of their Antimicrobial Activity

2016 ◽  
Vol 70 ◽  
pp. 1-11
Author(s):  
Neha N. Gohil ◽  
Kaushik N. Kundaliya ◽  
Dinkar I. Brahmbhatt
Keyword(s):  
Antimicrobial Activity ◽  
Fungal Pathogens ◽  
Sodium Acetate ◽  
Efficient Synthesis ◽  
Mass Spectral Data ◽  
Pyridinium Bromide ◽  
Mass Spectral ◽  
H Nmr ◽  
Anti Fungal ◽  
C Nmr

A series of novel [1,2,3]-triazolyl substituted benzo [c] coumarins have been synthesized by reacting various 3-coumarinoyl methyl pyridinium bromide salts with 1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl) ethanones in the presence of sodium acetate in refluxing acetic acid. The structures of the synthesized compounds have been elucidated by IR,1H-NMR,13C-NMR and Mass spectral data. All the synthesized compounds have been screened for theirinvitroanti-bacterial and anti-fungal activities. Some of the compounds have been found to be active against some bacterial and fungal pathogens compared to standard drugs.

2-Amino-substituted derivatives of benzimidazoles from 2-isothiocyanato carboxylates

1989 ◽  
Vol 54 (1) ◽  
pp. 206-214 ◽  
Author(s):  
Ľubomír Floch ◽  
Michal Uher ◽  
Ján Leško
Keyword(s):  
Spectral Methods ◽  
Mass Spectral ◽  
Derivatives Of ◽  
C Nmr

2-Isothiocyanato carboxylates react with o-phenylenediamine to give N,N'-substituted thioureas, which cyclize to yield 2-amino-substituted derivatives of imidazole. The structure of these compounds was corroborated by IR, UV, 1H, 13C NMR, and mass spectral methods.

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