One-pot four component domino strategy for the synthesis of novel spirooxindole pyrrolizine linked 1,2,3-triazoles via stereo- and regioselective [3 + 2] cycloaddition reaction in acidic medium

An efficient, one-pot four component condensation has been reported for the synthesis of spirooxindole pyrrolizine linked 1,2,3-triazolesvia[3 + 2] cycloaddition. The structures were confirmed by1H NMR,13C NMR, mass spectra and X-ray.

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Efficient continuous flow-synthesis of novel spiro-naphthalene-1,2'-[1,3,4]oxadiazol-4-ones

10.3762/bxiv.2021.89.v1 ◽

2021 ◽

Author(s):

Lange Yakubu Saleh ◽

Bahadır Altıntaş ◽

Layla Filiciotto ◽

Yunus Zorlu ◽

Rafael Luque ◽

...

Keyword(s):

Quantum Chemical ◽

Cycloaddition Reaction ◽

Synthesis Methods ◽

X Ray Diffraction ◽

Flow Synthesis ◽

X Ray ◽

H Nmr ◽

Experimental Findings ◽

Hydrazonyl Chlorides ◽

C Nmr

The highly efficient cycloaddition reaction of hydrazonyl chlorides with 2,3-dichloro-1,4-naphthoquinone yielded pharmaceutically important spiro-naphthalene-1,2'-[1,3,4]oxadiazol-4-ones with moderate to good yields under batch and flow synthesis methods. The obtained products were elucidated by IR, 1H NMR, 13C NMR, HRMS and single crystal X-ray diffraction technique (only for 6h). The synthesized molecules have been subjected to theoretical analysis by quantum chemical calculations at B3LYP/6-31G(d,p) level, which provided supporting data for the experimental findings.

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Synthesis and Pharmacological Evaluation of a Novel Series of Cyclopentenone Derivatives

Journal of Chemical Research ◽

10.3184/174751917x14837116219654 ◽

2017 ◽

Vol 41 (1) ◽

pp. 50-56 ◽

Cited By ~ 1

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.

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3-pyridiniumindolyl-2-thiolates - New type of functionalized indoles

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19881761 ◽

1988 ◽

Vol 53 (8) ◽

pp. 1761-1769 ◽

Cited By ~ 6

Author(s):

Jozef Gonda ◽

Pavol Kristian

Keyword(s):

Diffraction Analysis ◽

Dimethyl Sulfoxide ◽

Mass Spectra ◽

Sodium Ethoxide ◽

Sodium Hydride ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

New Type ◽

C Nmr

2-Bromomethylphenyl isothiocyanate (I) reacts with pyridines to give 2-isothiocyanatobenzylpyridinium bromides II. Deprotonation of these compounds with sodium ethoxide in ethanol of sodium hydride in dimethyl sulfoxide afforded novel type of functionalized indoles, 3-pyridiniumindolyl-2-thiolates. Reaction of II with KOH or KCN gave products of addition to the NCS group VII and VIII, respectively. Structure of the obtained compounds was proven by IR, 1H NMR, 13C NMR, and mass spectra and was confirmed by X-ray diffraction analysis of 3-pyridiniumindolyl-2-thiolate.

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

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19833426 ◽

1983 ◽

Vol 48 (12) ◽

pp. 3426-3432 ◽

Cited By ~ 4

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.

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

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19800548 ◽

1980 ◽

Vol 45 (2) ◽

pp. 548-558 ◽

Cited By ~ 7

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.

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[Zn(phen)2(CX3COO)]+, X = H orCl; Influence of X on the Coordination Mode of the Carboxylate Group (phen = 1,10-Phenanthroline)

Zeitschrift für Naturforschung B ◽

10.1515/znb-2005-1005 ◽

2005 ◽

Vol 60 (10) ◽

pp. 1049-1053 ◽

Cited By ~ 1

Author(s):

Zeanab Talaei ◽

Ali Morsali ◽

Ali R. Mahjoub

Keyword(s):

Nmr Spectroscopy ◽

Elemental Analysis ◽

Coordination Mode ◽

Bidentate Ligand ◽

Carboxylate Group ◽

X Ray ◽

X Ray Crystallography ◽

H Nmr ◽

Coordinate Geometry ◽

C Nmr

Two new ZnII(phen)2 complexes with trichloroacetate and acetate anions, [Zn(phen)2(CCl3COO)- (H2O)](ClO4) and [Zn(phen)2(CH3COO)](ClO4), have been synthesized and characterized by elemental analysis, IR, 1H NMR, 13C NMR spectroscopy. The single crystal X-ray data of these compounds show the Zn atoms to have six-coordinate geometry. From IR spectra and X-ray crystallography it is established that the coordination of the COO− group is different for trichloroacetate and acetate. The former acts as a monodentate whereas the latter acts as a bidentate ligand.

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Crystal structure of 3-chlorobenzo[b]thiophene-2-carbonyl chloride

Journal of Chemical Research ◽

10.3184/030823409x466041 ◽

2009 ◽

Vol 2009 (7) ◽

pp. 437-439 ◽

Cited By ~ 1

Author(s):

Sara Tarighi ◽

Alireza Abbasi ◽

Sara Zamanian ◽

Alireza Badiei ◽

Mahmood Ghoranneviss

Keyword(s):

Crystal Structure ◽

Mass Spectrometry ◽

Cinnamic Acid ◽

Thionyl Chloride ◽

Structure Determination ◽

X Ray ◽

Packing Structure ◽

H Nmr ◽

Carbonyl Chloride ◽

C Nmr

3-Chlorobenzo[b]thiophene-2-carbonyl chloride was synthesised from cinnamic acid and thionyl chloride. The single crystal X-ray structure determination confirmed the earlier proposed structure and the product was further characterised by 1H NMR, 13C NMR and mass spectrometry. The X-ray structure determination revealed two sets of symmetry related molecules along the b-axis that are loosely connected by relatively weak CH…π ( 3.626, 3.628 Å) interactions, giving rise to two infinite chains. The packing structure is dominated by Van der Waals forces between these chains. No significant π–π interactions are found in the crystal structure.

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Reactions of 3-(p-substituted-phenyl)-5-chloromethyl-1,2,4-oxadiazoles with KCN leading to acetonitriles and alkanes via a non-reductive decyanation pathway

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.14.280 ◽

2018 ◽

Vol 14 ◽

pp. 3011-3017

Author(s):

Akın Sağırlı ◽

Yaşar Dürüst

Keyword(s):

Nmr Spectra ◽

2D Nmr ◽

Synthetic Route ◽

X Ray ◽

H Nmr ◽

2D Nmr Spectra ◽

Tof Ms ◽

C Nmr

The present work describes an unfamiliar reaction of 5-(chloromethyl)-3-substituted-phenyl-1,2,4-oxadiazoles with KCN affording trisubstituted 1,2,4-oxadiazol-5-ylacetonitriles and their parent alkanes, namely, 1,2,3-trisubstituted-1,2,4-oxadiazol-5-ylpropanes. To the best of our knowledge, the current synthetic route leading to decyanated products will be the first in terms of a decyanation process which allows the transformation of trisubstituted acetonitriles into alkanes by the incorporation of KCN with the association of in situ-formed HCN and most likely through the extrusion of cyanogen which could not be detected or isolated. In addition, the plausible mechanisms were proposed for both transformations. The structures of the title compounds were identified by means of IR, 1H NMR, 13C NMR, 2D NMR spectra, TOF–MS and X-ray measurements.

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A series of Mn(i) photo-activated carbon monoxide-releasing molecules with benzimidazole coligands: synthesis, structural characterization, CO releasing properties and biological activity evaluation

RSC Advances ◽

10.1039/c9ra01370a ◽

2019 ◽

Vol 9 (36) ◽

pp. 20505-20512 ◽

Cited By ~ 1

Author(s):

Mixia Hu ◽

YaLi Yan ◽

Baohua Zhu ◽

Fei Chang ◽

Shiyong Yu ◽

...

Keyword(s):

Carbon Monoxide ◽

Biological Activity ◽

Activated Carbon ◽

Fluorescence Spectroscopy ◽

Single Crystal ◽

Structural Characterization ◽

X Ray Diffraction ◽

X Ray ◽

H Nmr ◽

C Nmr

Five Mn(i) photo-activated carbon monoxide-releasing molecules were synthesized by reactions of MnBr(CO)5 with L1–L4, and characterized via single crystal X-ray diffraction, 1H-NMR, 13C-NMR, IR, UV-vis and fluorescence spectroscopy.

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Chemie polyfunktioneller Moleküle, 114 [1]. Synthese und Struktur eines ionischen und nichtionischen, cyclischen Carbaphosphazens und eines Cobalt(III)phosphazen-Komplexes / Chemistry of Polyfunctional Molecules, 114 [1]. Synthesis and Structure of an Ionic and Non Ionic Cyclic Carbaphosphazene and of a Cobalt(III)phosphazene Complex

Zeitschrift für Naturforschung B ◽

10.1515/znb-1994-1222 ◽

1994 ◽

Vol 49 (12) ◽

pp. 1763-1773 ◽

Cited By ~ 6

Author(s):

Jochen Ellermann ◽

Jörg Sutter ◽

Falk A. Knoch ◽

Matthias Moll ◽

Walter Bauer

Keyword(s):

Mass Spectra ◽

Monoclinic Space Group ◽

Triclinic Space Group ◽

Space Group ◽

X Ray ◽

Lattice Constants ◽

H Nmr

Reaction of (1) in CH2Cl2 with benzimidazole yields . The salt [4]+BPh4- has been prepared in THF by metathesis of [4]+Cl- with NaBPh4. Deprotonation of the cationic ring in [4]+BPh4- was accomplished using 1,8-diazabicyclo[5.4.01,7]undec-7-ene and resulted in the six-membered carbacyclophosphazene (6). Treating 1 with 8 -hydroxyquinoline in CH2Cl2 yields the octahedral cis-complex = 8-oxyquinolinate group). The com pounds [4]+BPh4-, 6 and 7 are characterized by their IR, Raman, 31P{1H} NMR, 13C{1H} NMR, 1H NMR and mass spectra. Crystals suitable for X-ray structure analyses have been obtained for [4]+BPh4- and 7×0.5 CH2Cl2. The colourless plates of [4]+BPh4- crystallize in the triclinic space group P1̄, with the lattice constants a = 1172.7(3), b = 1326.2(3), c = 1806.1(6) pm; α = 100.79(2), β = 103.71(3), γ = 108.18(2)°. The black blocks of 7×0.5 CH2Cl2 crystallize in the monoclinic space group P 21/c with the lattice constants a = 1159.0(10), b = 2008.9(10), c = 2034.6(12) pm; β = 105.86(5)°.

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