Heterocyclisation of substituted ylidenethiocarbonohydrazides using dimethyl acetylenedicarboxylate

2015 ◽  
Vol 69 (7) ◽  
Author(s):  
Alaa A. Hassan ◽  
Fathy F. Abdel-Latif ◽  
Mohamed Abdel Aziz ◽  
Sara M. Mostafa ◽  
Stefan Bräse ◽  
...  
Keyword(s):  
Single Crystal ◽  
Condensation Reaction ◽  
Dimethyl Acetylenedicarboxylate ◽  
Rapid Procedure ◽  
X Ray

AbstractA facile and rapid procedure for the synthesis of dimethyl-2-[3-amino-5-(2-methoxy-2-oxoethylidene)- 4-oxothiazolidin-2-ylidenehydrazono]succinate, dimethyl {[2-alkylidenehydrazono)-5-(2-methoxy- 2-oxoethylidene)-4-oxothiazolidin-3-yl)amino]succinate and methyl (4-amino-5-oxo-3- thioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-yl)acetate affording yields of 61-54 %, 22-18 % and 14- 11 %, respectively, via a condensation reaction of dimethyl acetylenedicarboxylate (DMAD) with (substituted ylidene)thiocarbonohydrazides. One of the products was conclusively confirmed by single-crystal X-ray analysis. A mechanism for the formation of the products is presented.

Corroles in 1,3-dipolar cycloaddition reactions

2009 ◽  
Vol 13 (03) ◽  
pp. 358-368 ◽  
Author(s):  
Luís S. H. P. Vale ◽  
Joana F. B. Barata ◽  
Carla I. M. Santos ◽  
Maria G. P. M. S. Neves ◽  
Maria A. F. Faustino ◽  
...  
Keyword(s):  
Single Crystal ◽  
Diffraction Analysis ◽  
Dimethyl Fumarate ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray Diffraction ◽  
X Ray ◽  
Dipolar Cycloadditions ◽  
Pyridine Complex

The azomethine ylide generated from the reaction of a corrole-3-carbaldehyde and N-methylglycine was trapped with dimethyl fumarate, dimethyl acetylenedicarboxylate and fullerene C60 in 1,3-dipolar cycloadditions. A similar azomethine ylide generated from a corrole-2-carbaldehyde was trapped with 1,4-naphthoquinone, yielding the expected dehydrogenated 1,3-dipolar cycloadduct and a quinone-fused corrole derivative. A detailed synchrotron single-crystal X-ray diffraction analysis of the gallium(III)(pyridine) complex of 5,10,15-tris(pentafluorophenyl)corrole-3-carbaldehyde is also presented.

Spiro fused β-lactam cyclopropenes

1992 ◽  
Vol 70 (12) ◽  
pp. 2967-2971 ◽  
Author(s):  
Michel Zoghbi ◽  
John Warkentin
Keyword(s):  
Molecular Structure ◽  
Single Crystal ◽  
Strain Energy ◽  
High Strain ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray Diffraction ◽  
Cyclopropene Ring ◽  
X Ray ◽  
Lactam Ring ◽  
High Strain Energy

Δ3-1,3,4-Oxadiazolines (1) that share their C2 with C4 of a β-lactam ring in a spiro fusion were prepared. The structures were established through single crystal X-ray diffraction of 1a and by infrared, 1H, and 13C nuclear magnetic resonance spectroscopies. Thermolysis of 1 at 100 °C, in benzene containing dimethyl acetylenedicarboxylate, afforded spiro-fused β-lactam cyclopropene 12 in 33% yield. Similar thermolysis of 1b in the presence of ethyl phenylpropiolate gave spiro-fused β-lactam cyclopropene 13 (32%). The molecular structure of 12, determined by single crystal X-ray diffraction, has the two ester carbonyl carbons out of the plane of the cyclopropene ring by about 0.17 Ǻ, indicating substantial nonbonded steric interactions and suggesting unusually high strain energy. At 154.5 °C, 12 underwent isomerization to 19, presumably through a vinyl carbene intermediate.

Cycloaddition Reactions of 3-Dimethylamino-1-methyl-1,2,4-triazinium-5-olates With Dimethyl Acetylenedicarboxylate

1995 ◽  
Vol 48 (6) ◽  
pp. 1175 ◽  
Author(s):  
RP Musgrave ◽  
NW Jacobsen ◽  
G Bourne ◽  
CHL Kennard ◽  
G Smith ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Single Crystal ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
Structure Determinations ◽  
Mechanism Of The Reaction

The cycloaddition reactions of some 3-dimethylamino-1-methyl-1,2,4-triazinium-5-olates (1) with dimethyl acetylenedicarboxylate ( dmad ) were studied. The products in all cases were found tobe dimethyl 4-dimethylamino-1-methyl-6-oxo-1,3a,6,6a-tetrahydropyrrolo[3,4-c]pyrazole-3,3a-dicarboxylate derivatives (2). The structure determinations were carried out by 1H and 13C n.m.r. and mass spectrometry, and for one derivative by single-crystal X-ray diffractometry. The mechanism of the reaction is also discussed.

scholarly journals X-ray structure of hexamethyl benzenehexacarboxylate, [C6(COOCH3)6]

1970 ◽  
Vol 34 (2) ◽  
pp. 197-200
Author(s):  
Shishir Ghosh ◽  
Md Kamal Hossain ◽  
Shariff E Kabir ◽  
Noorjahan Begum
Keyword(s):  
Thermal Treatment ◽  
Single Crystal ◽  
Diffraction Study ◽  
Key Words ◽  
Spectroscopic Data ◽  
Monoclinic Space Group ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray Diffraction ◽  
X Ray ◽  
Academy Of Sciences

The thermal treatment of [Ru2(CO)6(μ-η1,η2-C4H3O){μ-P(C4H3O)2}] 1 with dimethyl acetylenedicarboxylate (DMAD) at 110 °C leads to cyclotrimerization of DMAD. The cyclotrimerization product hexamethyl benzenehexacarboxylate, [C6(COOCH3)6] 2, was obtained in 37% yield and characterized by a combination of spectroscopic data and single crystal X-ray diffraction study. Compound 2 crystallizes in the monoclinic space group P1bar with a = 10.3002(12), b = 11.0371(13), c = 18.781(2) Å, α = 76.148(2), β = 87.390(2), γ = 74.001(2)°, Z = 4 and V = 1992.2(4) Å3. Key words: Cyclotrimerization; Dimethyl acetylenedicarboxylate; X-ray structure DOI: 10.3329/jbas.v34i2.6866Journal of Bangladesh Academy of Sciences, Vol. 34, No. 2, 197-200, 2010

Diels-Alder additions of dimethyl acetylenedicarboxylate to sterically hindered cyclohexa-2,4-dienones. Formation and X-ray structure analysis of stereoisomeric bicyclo[2.2.2]octadienones

1983 ◽  
Vol 36 (7) ◽  
pp. 1361 ◽  
Author(s):  
H Becker ◽  
BW Skelton ◽  
AH White
Keyword(s):  
Single Crystal ◽  
Structure Analysis ◽  
Electronic Absorption ◽  
Spectral Properties ◽  
Diels Alder ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray Diffraction ◽  
X Ray ◽  
Sterically Hindered

The Diels-Alder addition of dimethyl acetylenedicarboxylate to sterically hindered 2,4-cyclohexadienones (spiro-quinol ethers) gives rise to stereoisomeric bicyclo[2.2.2]octadienones. The structures of three of these have been elucidated by single-crystal X-ray diffraction methods and their 1H n.m.r. and electronic absorption spectral properties are reported.

scholarly journals Reaction of a 3-aryilidene-2-thiohydantoin derivative with polymeric trans-[CuCl2(DMSO)2]n complex: Unexpected isomerization to dinuclear cis-[{CuCl(DMSO)2}(μ-Cl)]2

2020 ◽  
pp. 60-60
Author(s):  
Petar Stanic ◽  
Marko Rodic ◽  
Tanja Soldatovic ◽  
Aleksandar Pavic ◽  
Natasa Radakovic ◽  
...  
Keyword(s):  
Ir Spectroscopy ◽  
Single Crystal ◽  
Diffraction Analysis ◽  
Elemental Analysis ◽  
Crucial Role ◽  
Condensation Reaction ◽  
X Ray Diffraction ◽  
Trans Form ◽  
X Ray ◽  
Stable Product

The 3-arylidene-2-thiohydantoin derivative, 3-[(2-hydroxybenzyl-idene)amino]-2-thioxoimidazolidin-4-one, was synthesized in a two-step condensation reaction of 2-hydroxybenzaldehyde, thiosemicarbazide and ethyl chloroacetate. The ligand was structurally characterized by NMR and IR spectroscopy, as well as elemental analysis. In the reaction of the well-known polymeric trans-[CuCl2(DMSO)2]n complex with the polydentate thiohydantoin type ligand, instead of the corresponding copper thiohydantoin complex, unexpectedly, the dinuclear cis-[{CuCl(DMSO)2}(m-Cl)]2 complex (1) was formed predominantly as the final stable product. The structure of the complex 1 was confirmed by single crystal X-ray diffraction analysis. The cis-complex is obtained through assisted isomerization of the trans-form, in which the thiohydantoin derivative has a crucial role.

scholarly journals Synthesis, Characterization, Crystallographic Studies of 5-Acetyl-8-hydroxyquinoline and Their Chalcone Derivatives

2020 ◽  
Vol 32 (7) ◽  
pp. 1609-1613
Author(s):  
C.B. Vagish ◽  
Karthik Kumara ◽  
N.K. Lokanath ◽  
K. Ajay Kumar ◽  
P.G. Chandrasherkar
Keyword(s):  
Single Crystal ◽  
Benzoyl Chloride ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Spectral Studies ◽  
Monoclinic Crystal System ◽  
X Ray Diffraction ◽  
Monoclinic Crystal ◽  
One Pot ◽  
X Ray

An efficient, easy and one pot synthesis for the Friedel-Craft acetylation reaction of quinolines was developed. The reaction between 8-hydroxyquinoline and acetyl/benzoyl chloride in nitrobenzene immediately flocculates as yellow precipitate. On further addition of Lewis acid causes the Friedel-Craft acetylation leads to formation of acetylated quionlines in good yields. The structure of compound 5-acetyl-8-hydroxyquinoline (3) was confirmed by single crystal X-ray diffraction studies. The compound crystallizes in the monoclinic crystal system with the space group P21/c. The synthesized acetylated quionlines undergoes condensation reaction with aromatic aldehydes leads to 8-hydroxyquinoline chalcones derivatives. The products were characterized by spectral studies, elemental analysis and single crystal X-ray diffraction studies.

scholarly journals Utilization of 1-phenylimidazo[1,5-a]quinoline as partner in 1,4-dipolar cycloaddition reactions

2020 ◽  
Vol 75 (3) ◽  
pp. 259-267
Author(s):  
Areej M. Jaber ◽  
Jalal A. Zahra ◽  
Mustafa M. El-Abadelah ◽  
Salim S. Sabri ◽  
Monther A. Khanfar ◽  
...  
Keyword(s):  
Single Crystal ◽  
Spectral Data ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
X Ray Crystallography

AbstractA Selected set of 2-(quinolin-2-yl)-1,3-oxazepino[7,6-b]indoles 4a–d and dihydroacenaphtho[1,2-f][1,3]oxazepine 5 have been prepared via 1,4-dipolar cycloaddition reaction involving 1-phenylimidazo[1,5-a]quinoline, dimethyl acetylenedicarboxylate, and N-(substituted)isatins or acenaphthoquinone. Structures of the new heterocycles 4a–d and 5 are supported by NMR and HRMS spectral data, and confirmed by single-crystal X-ray crystallography for 4c and 5.

Heterocycles 21. Reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Valentin Zaharia ◽  
Anca Silvestru ◽  
Philippe Verite ◽  
Mircea Vlassa ◽  
Silvia Imre ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Infrared Spectroscopy ◽  
Acetic Anhydride ◽  
Single Crystal ◽  
Condensation Reaction ◽  
Spectroscopic Methods ◽  
X Ray Diffraction ◽  
Basic Catalysis ◽  
X Ray ◽  
Diffraction Structure

The condensation reaction of 2-phenyl-thiazol-4-carbaldehyde with 2-bromoacetophenone was performed in basic catalysis, resulting in a mixture of 2,3-epoxy-1-phenyl-3-(2-phenyl-thiazol-4-yl)-propan-1-one (1), 1-phenyl-3-(2-phenyl-thiazol-4-yl)-propane-1,2-dione (2) and 2-phenyl-4,5-bis-(2-phenyl-thiazol-4-yl)-3-hydroxy-furane (4). The isolated solids were structurally investigated by spectroscopic methods, i.e. infrared spectroscopy, mass spectrometry and NMR. In solution the dicarbonylic derivative 2 undergoes a tautomeric process, resulting in the enol 2-hydroxy-1-phenyl-3-(2-phenyl-thiazol-4-yl)-prop-2-en-1-one 3. Compounds 3 and 4 were transformed in the corresponding acetyl derivatives 5 and 6, respectively, by reacting them with acetic anhydride. For the furane 4 the single crystal X-ray diffraction structure was determined.

Synthesis of bis-thiazolidin-4-ones from N,N,N″-(1,ω-alkanediyl)bis(N″-organylthiourea) derivatives

2015 ◽  
Vol 70 (4) ◽  
pp. 243-248 ◽  
Author(s):  
Alaa A. Hassan ◽  
Kamal M.A. El-Shaieb ◽  
Amal S. Abd El-Aal ◽  
Stefan Bräse ◽  
Martin Nieger
Keyword(s):  
Single Crystal ◽  
Spectroscopic Data ◽  
Dimethyl Acetylenedicarboxylate ◽  
X Ray ◽  
X Ray Crystallography ◽  
Elemental Analyses

AbstractA new series of (2Z,2′E)-dimethyl 2,2′-[(2Z,2′Z)-3,3′-(alkanediyl)bis(4-oxo-2-iminothiozolidin-3-yl-5-ylidene)]acetates has been synthesized by the reaction of N,N″-(1,ω-alkanediyl)bis(N′-organylthiourea) derivatives with dimethyl acetylenedicarboxylate. The structures were established by spectroscopic data, elemental analyses, and single crystal X-ray crystallography. A rationale for the formation of the products is presented.

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