Michael-Michael Aldol Reaction of Chalcones with Cyanoacetylurea and Cyanoacetylpiperidine

A series of heterocyclic hypervalent (HV) iodine(III) compounds containing fused tetrazole and benziodazole rings, i.e., derivatives of benziodazolotetrazole (BIAT) with various ligands (L) attached to the iodine atom (BIAT-L) were prepared and studied. They were characterized by 1H and 13C NMR spectroscopy, ESI-HRMS, and X-ray crystallography. The thermal stabilities of all BIAT derivatives (L= Cl, OH, OAc, OMe) were studied and the degradation patterns as well as the enthalpies of degradation were measured by thermal gravimetric analysis coupled with differential scanning calorimetry. The reaction of various alkenes with BIAT-Cl in the presence of Cu(OTf)2 at room temperature yielded chloro-tetrazolylated products. The oxidation of thioanisole with BIAT-Cl under various reaction conditions is also reported.

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Diastereoselective One-Pot Tandem Synthesis of Chromenopyridodiazepinones through 1,4- and 1,6-Aza-Conjugate Additions/Heterocyclizations

Synlett ◽

10.1055/s-0037-1609201 ◽

2018 ◽

Vol 29 (07) ◽

pp. 885-889 ◽

Cited By ~ 1

Author(s):

Oualid Talhi ◽

Artur Silva ◽

Abdelghani Bouchama ◽

Ridha Hassaine ◽

Nadia Taibi ◽

...

Keyword(s):

Room Temperature ◽

Amino Group ◽

Conjugate Additions ◽

One Pot ◽

X Ray ◽

X Ray Crystallography ◽

Mild Conditions ◽

Reaction Proceeds ◽

Tandem Process ◽

Tandem Synthesis

We report an efficient one-pot synthesis of a novel series of chromenopyridodiazepinone polyheterocycles by a catalyst-free nucleophilic addition of ethane-1,2-diamine to (E,E)-3-[3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl]-2-styrylchromones at room temperature under mild conditions. The reaction proceeds by a tandem process involving 1,4- and 1,6-aza-conjugate additions of one amino group of ethane-1,2-diamine to the α,β-unsaturated (3-oxoprop-1-en-1-yl) and the α,β,γ,δ-diunsaturated (2-styrylchromone) carbonyl system of the precursor, followed by imine condensation of the remaining amino group to generate the chromenopyridodiazepinone polyheterocycle. All compounds were characterized by means of one- and two-dimensional NMR spectroscopy and single-crystal X-ray crystallography.

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Synthesis and X-ray powder diffraction data of cis-4-(4-methoxyphenyl)-3-methyl-6-nitro-2-phenyl-1,2,3,4-tetrahydroquinoline

Powder Diffraction ◽

10.1017/s0885715613000651 ◽

2013 ◽

Vol 28 (4) ◽

pp. 307-311 ◽

Cited By ~ 1

Author(s):

M.A. Macías ◽

J.A. Henao ◽

Arnold R. Romero Bohórquez ◽

Vladimir V. Kouznetsov

Keyword(s):

Powder Diffraction ◽

Alder Reaction ◽

Diels Alder ◽

Gas Chromatography Mass Spectrometry ◽

One Pot ◽

X Ray ◽

Cell Parameters ◽

Diels Alder Reaction ◽

The One ◽

C Nmr

The 2,4-diaryl 1,2,3,4-tetrahydroquinoline derivative (1), described in the title (Chemical formula: C23H22N2O3), was synthesized via the “one-pot” three-component imino Diels–Alder reaction catalyzed by Cu(OTf)2. Molecular characterization was performed by 1H and 13C NMR, Fourier transform-infrared, and gas chromatography-mass spectrometry. The X-ray powder diffraction pattern for the title compound was analyzed and found to be crystallized in an orthorhombic system with space group P212121 (No. 19) and refined unit-cell parameters a = 8.6415(8) Å, b = 12.679(2) Å, c = 17.601(2) Å, and V = 1928.4(2) Å3.

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Synthesis and Characterization of Unsymmetrical Double-Decker Siloxane (Basket Cage)

Molecules ◽

10.3390/molecules24234252 ◽

2019 ◽

Vol 24 (23) ◽

pp. 4252 ◽

Cited By ~ 3

Author(s):

Rungthip Kunthom ◽

Nobuhiro Takeda ◽

Masafumi Unno

Keyword(s):

29Si Nmr ◽

Cage Compounds ◽

One Pot ◽

X Ray ◽

X Ray Crystallography ◽

Double Decker ◽

Novel Structure ◽

The One ◽

First Time

The one-pot synthesis of an unsymmetrical double-decker siloxane with a novel structure via the reaction of double-decker tetrasodiumsilanolate with 1 equiv. of dichlorotetraphenyldisiloxane in the presence of an acid is reported herein for the first time. The target compound bearing all phenyl substituents on the unsymmetrical siloxane structure was successfully obtained, as confirmed by 1H-NMR, 13C-NMR, 29Si-NMR, IR, MALDI-TOF, and X-ray crystallography analyses. Additionally, the thermal properties of the product were evaluated by TG/DTA and compared with those of other siloxane cage compounds.

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Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.15.134 ◽

2019 ◽

Vol 15 ◽

pp. 1347-1354

Author(s):

Andrew T King ◽

Hugh G Hiscocks ◽

Lidia Matesic ◽

Mohan Bhadbhade ◽

Roger Bishop ◽

...

Keyword(s):

Single Crystal ◽

Unit Cell ◽

Unit Cell Parameters ◽

One Pot ◽

Space Group ◽

X Ray ◽

Cell Parameters ◽

X Ray Crystallography ◽

The One ◽

Close Contacts

The one-pot reaction of 2,6-bis(diphenylmethyl)-4-methoxyaniline with tert-butylnitrite, BTEAC and DABSO in the presence of CuCl2 provided an unexpected 3H-indazole product 8. The structure of the compound was determined by HRMS, IR, NMR and further confirmed by single crystal X-ray crystallography. The compound crystallises in the triclinic P-1 space group, with unit cell parameters a = 9.2107 (4), b = 10.0413 (5), c = 14.4363 (6) Å, α = 78.183 (2), β = 87.625 (2), γ = 71.975 (2)°. The formation of 8 proceeded through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate 9. The molecules of 8 are organised by edge–face Ar–H···π, face–face π···π, and bifurcated OCH2–H···N interactions. In addition to these, there are Ar–H···H–Ar close contacts, (edge–edge and surrounding inversion centres) arranged as infinite tapes along the a direction.

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Eco-Friendly Synthesis of 2-Substituted Benzimidazoles Using Air as the Oxidant

Australian Journal of Chemistry ◽

10.1071/ch12458 ◽

2013 ◽

Vol 66 (2) ◽

pp. 262 ◽

Cited By ~ 13

Author(s):

Guo-Feng Chen ◽

Hai-Dong Shen ◽

Hui-Ming Jia ◽

Li-Yan Zhang ◽

Hong-Yan Kang ◽

...

Keyword(s):

Room Temperature ◽

Environmentally Friendly ◽

Aromatic Aldehydes ◽

Absolute Ethanol ◽

One Pot ◽

Mild Conditions ◽

One Pot Condensation ◽

The One

A simple, environmentally friendly procedure for the synthesis of 2-substituted benzimidazoles by the one-pot condensation of o-phenylenediamines with aromatic aldehydes using continuous bubbling of air in absolute ethanol at room temperature is described. The simplicity of the system, mild conditions, involvement of a non-toxic and practically inexhaustible oxidant, easy and quick isolation of the products, and moderate to good yields are the main advantages of this procedure.

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Heterocyclic Hypervalent Iodine(III) Compounds with Fused Benziodazole and Tetrazole Rings (I-Substituted Tetrazolo[1,5-b][1,2]Benziodazoles)

10.26434/chemrxiv.13363496.v1 ◽

2020 ◽

Author(s):

Rajesh Kumar ◽

Kapil Dev Sayala ◽

Lejla Lejla Camdzic ◽

Maxime Siegler ◽

Avichal Vaish ◽

...

Keyword(s):

Room Temperature ◽

Hypervalent Iodine ◽

Gravimetric Analysis ◽

Scanning Calorimetry ◽

Reaction Conditions ◽

Thermal Stabilities ◽

X Ray ◽

X Ray Crystallography ◽

Derivatives Of ◽

C Nmr

A series of heterocyclic hypervalent (HV) iodine(III) compounds containing fused tetrazole and benziodazole rings, i.e., derivatives of benziodazolotetrazole (BIAT) with various ligands (L) attached to the iodine atom (BIAT-L) were prepared and studied. They were characterized by 1H and 13C NMR spectroscopy, ESI-HRMS, and X-ray crystallography. The thermal stabilities of all BIAT derivatives (L= Cl, OH, OAc, OMe) were studied and the degradation patterns as well as the enthalpies of degradation were measured by thermal gravimetric analysis coupled with differential scanning calorimetry. The reaction of various alkenes with BIAT-Cl in the presence of Cu(OTf)2 at room temperature yielded chloro-tetrazolylated products. The oxidation of thioanisole with BIAT-Cl under various reaction conditions is also reported.

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A topochemical rearrangement with multiple inversions of configuration

Canadian Journal of Chemistry ◽

10.1139/v01-099 ◽

2001 ◽

Vol 79 (8) ◽

pp. 1272-1277 ◽

Cited By ~ 1

Author(s):

Saul Wolfe ◽

Yih-Huang Hsieh ◽

Raymond J Batchelor ◽

Frederick WB Einstein ◽

Ian D Gay

Keyword(s):

Crystal Structure ◽

Solid State ◽

Room Temperature ◽

The Other ◽

X Ray ◽

Controlled Processes ◽

X Ray Crystallography ◽

Intramolecular Process ◽

C Nmr ◽

The Ideal

Crystalline 2-benzyloxypyridine-1-oxide rearranges slowly at room temperature to crystalline 1-benzyloxy-2-pyridone. No intermediates are detected when the process is followed by solid-state 13C NMR. The crystal structure of the pyridine-1-oxide strongly suggests that a topochemically controlled intramolecular process, in which the benzyl group migrates with retention of configuration, is not feasible. On the other hand, although somewhat disfavoured by initial solid-state O···C···O angles significantly less than the ideal 180°, intermolecular topochemically controlled processes can be envisaged that lead, with multiple inversions of configuration, either to net retention of configuration or to net inversion of configuration in the benzyl group. In contrast to the 5080% inversion observed in solution, in the solid state only inversion is observed experimentally when chirally labelled α-deuteriobenzyloxypyridine-1-oxide is allowed to rearrange.Key words: X-ray crystallography, solid-state 13C NMR, benzyl-α-D-alcohol, 2-benzyloxypyridine-1-oxide, 1-benzyloxy-2-pyridone.

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1-(2′-Benzimidazolylmethyl)-pyridinium ylide in the one-pot synthesis of indolizine and benzimidazo[1,2-a]pyridine derivatives

Zeitschrift für Naturforschung B ◽

10.1515/znb-2015-0016 ◽

2015 ◽

Vol 70 (8) ◽

pp. 555-561 ◽

Cited By ~ 5

Author(s):

Roumaissa Belguedj ◽

Sofiane Bouacida ◽

Hocine Merazig ◽

Ali Belfaitah ◽

Abdelmalek Bouraiou

Keyword(s):

Nmr Spectroscopy ◽

Cycloaddition Reaction ◽

Dipolar Cycloaddition ◽

Pyridine Derivatives ◽

One Pot ◽

X Ray ◽

X Ray Crystallography ◽

Dimethyl Maleate ◽

The One ◽

Pyridinium Ylide

AbstractFour indolizine derivatives were obtained via 1,3-dipolar cycloaddition reaction of 1-(2′-benzimidazolylmethyl)pyridinium ylide with various electron-deficient alkynes. The reaction of this pyridinium N-ylide with dimethyl maleate gave an unexpected methyl 1-oxo-benzimidazo[1,2-a]pyridine-3-carboxylate. The structures of all reported compounds have been examined by X-ray crystallography and NMR spectroscopy.

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A Series of Metal-Organic Frameworks for Selective CO2 Capture and Catalytic Oxidative Carboxylation of Olefins

10.26434/chemrxiv.7068509 ◽

2018 ◽

Author(s):

Huong T. D. Nguyen ◽

Y B. N. Tran ◽

Hung N. Nguyen ◽

Tranh C. Nguyen ◽

Felipe Gándara ◽

...

Keyword(s):

Room Temperature ◽

Gas Adsorption ◽

New Materials ◽

One Pot ◽

Acid Gas ◽

Naphthalene Diimide ◽

Styrene Carbonate ◽

Metal Organic ◽

Adsorption Of Co ◽

The One

Three novel lanthanide metal˗organic frameworks (Ln-MOFs), namely MOF-590, -591, and -592 were constructed from a naphthalene diimide tetracarboxylic acid. Gas adsorption measurements of MOF-591 and -592 revealed good adsorption of CO2 (low pressure, at room temperature) and moderate CO2 selectivity over N2 and CH4. Accordingly, breakthrough measurements were performed on a representative MOF-592, in which the separation of CO2 from binary mixture containing N2 and CO2 was demonstrated without any loss in performance over three consecutive cycles. Moreover, MOF-590, MOF-591, and MOF-592 exhibited catalytic activity in the one-pot synthesis of styrene carbonate from styrene and CO2 under mild conditions (1 atm CO2, 80 °C, and solvent-free). Among the new materials, MOF-590 revealed a remarkable efficiency with exceptional conversion (96%), selectivity (95%), and yield (91%).

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