Stereospecific Synthesis of 4,8-Dimethylspiro(4,5)-deca-7-ene-1,6-dione A Synthetic Route to the Acoranes

1983 ◽  
Vol 38 (4) ◽  
pp. 497-500 ◽  
Author(s):  
E. L. Michelotti ◽  
E. L. Sanchez

Abstract A stereospecific synthesis of 4,8-dimethylspiro(4,5)-deca-7-ene-1,6-dione from 4,7-dimethylcoumarine in high yield is reported. The configuration of this product is established according to its 1H NMR and 13C NMR data.

1997 ◽  
Vol 62 (8) ◽  
pp. 1254-1262 ◽  
Author(s):  
Bernd Wrackmeyer ◽  
Hans-Jörg Schanz

The formation of organo substituted 1-carba-arachno-pentaborane(10) derivatives is shown to proceed in high yield via in situ generated 1,1,1-tris(diethylboryl)propane (2) from diethyl(propyn-1-yl)borane (1) by hydroboration with an excess of diethylborane (hydride bath). In the hydride bath, exchange reactions between 2 and other geminal bis(diethylboryl)alkanes take place until the carbaborane skeleton is formed. If tris(diethylboryl)methane is used under the same conditions, the corresponding 1-carba-arachno-pentaborane(10) derivatives 11 and 12 are formed in mixture with other unknown boranes or carboranes. 11B and 13C NMR data are presented to allow for straightforward identification of the 1-carba-arachno-pentaboranes(10).


2012 ◽  
Vol 9 (3) ◽  
pp. 1518-1525 ◽  
Author(s):  
Hamid Reza Jaberi ◽  
Hadi Noorizadeh

In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR,1H NMR and13C NMR data.


2018 ◽  
Vol 14 ◽  
pp. 3011-3017
Author(s):  
Akın Sağırlı ◽  
Yaşar Dürüst
Keyword(s):  
2D Nmr ◽  
X Ray ◽  
H Nmr ◽  
Tof Ms ◽  

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.


2011 ◽  
Vol 2011 ◽  
pp. 1-6 ◽  
Author(s):  
Shao Han Liao ◽  
Dai Hua Hu ◽  
Ai Ling Wang ◽  
De Peng Li

As core skeletons of lamellarins: 5,6-Dihydropyrrolo[2,1-a]isoquinolines are one of the important alkaloids that exhibit significant biological activities, in this study, an efficient synthetic route was described for two novel compounds, 5,6-dihydropyrrolo[2,1-a]isoquinolinesIandII. CompoundIwas synthesized from isovanillin with 28.3% overall yield by a six-step reaction whileIIfrom 2-(3,4-dimethoxyphenyl) ethanamine was with 61.6% overall yield by a three-step reaction. And the structures of these two compounds were confirmed by means of IR spectrum,1H NMR,13C NMR, MS, HRMS, and melting point measurements.


2012 ◽  
Vol 2012 ◽  
pp. 1-7 ◽  
Author(s):  
Varadhan Krishnakumar ◽  
Kesarla Mohan Kumar ◽  
Badal Kumar Mandal ◽  
Fazlur-Rahman Nawaz Khan

The diversified bis-isoquinolinones were obtained in two steps, utilizing homophthalic acid and various acid chlorides providing 3-substituted isocoumarins in the first step which on further condensation with 1,7-heptadiamine involving C–N bond formation from the lactone in the presence of 10 mol% zinc oxide nanoparticles (ZnO NPs) (<150 nm) afforded the desired bis-isoquinolinones in high yield and purity. The synthesized compounds were then characterized using FTIR,1H NMR,13C NMR, and HRMS techniques.


1981 ◽  
Vol 46 (6) ◽  
pp. 1474-1485 ◽  
Author(s):  
František Tureček ◽  
Vladimír Hanuš ◽  
Petr Sedmera ◽  
Helena Antropiusová ◽  
Karel Mach

Dimerization of cycloheptatriene, catalyzed by titanium complexes, afforded pentacyclo[8.4.0.03,7.04,14.06,11]tetradeca-8,12-diene (I) (10%) and pentacyclo[7.5.0.02,8.05,14.07,11]tetradeca-3,12-diene (II) (90%). Structure of both dimers and their derivatives was determined by means of 1H NMR, 13C NMR and mass spectra. On heating, the diene II was converted into the more stable isomer I. On hydrogenation and further catalytic isomerization, both I and II gave diamantane in high yield.


2014 ◽  
Vol 33 (2) ◽  
pp. 189 ◽  
Author(s):  
Mustafa Er ◽  
Ayşe Şahin ◽  
Hakan Tahtacı

<p>Thiosemicarbazone derivatives <strong>3a–e</strong> were synthesized by the reaction of various aldehydes<strong> 1a–e</strong> with 4-methyl thiosemicarbazide <strong>2</strong> in 78% to 90% yield. Then, the thiazole moieties of the target materials <strong>5a–e</strong> were obtained in high yields (71–93%) using the Hantzsch reaction utilizing thiosemicarbazone derivatives <strong>3a–e</strong> with ethyl-2-chloroacetoacetic ester. The substituted nitrile derivatives <strong>7a–e</strong> were obtained in moderate to high yield (58–84%) from the reaction of compounds <strong>5a–e</strong> with chloroacetonitrile by the nucleophilic aliphatic substitution reaction in the presence of anhydrous potassium carbonate. Finally, substituted 2-amino-1,3,4-thiadiazole compounds <strong>9a–e</strong> were obtained in moderate to good yields (51–62%) from the reaction of thiosemicarbazide with substituted nitrile derivatives <strong>7a–e</strong>. As a result, compounds that all share a high disposition for biological activities were obtained. The structures of the newly synthesized compounds were confirmed by IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, elemental analysis, and mass spectrometric techniques.</p>


Author(s):  
Haresh G. Kathrotiya ◽  
Yogesh T. Naliapara

A new series of thiophenyl thiazole based novel quinoxaline derivatives 4a-4t have been synthesized by base catalysed condensation reaction. In which 6-substituted 2,3-dichloroquinoxaline 1a and 4-(thiophen-2-yl) thiazol-2-amine 2b reacted in basic condition to afford intermediate 3c which reacts with various aromatic amine to form final compounds. Easy experimental procedure, high yield, and selectivity are the imperative features of this method. The identity of all the compounds has been established by 1H NMR, 13C NMR, FT-IR, and elemental analysis.


1982 ◽  
Vol 37 (12) ◽  
pp. 1661-1664 ◽  
Author(s):  
Martin Feigel ◽  
Gerhard Hägele ◽  
Axel Hinke ◽  
Gudrun Tossing

2D NMR ist used to determine the 1H NMR parameters of L-Menthyldichlorophosphine. 13C NMR data are given


1988 ◽  
Vol 53 (7) ◽  
pp. 1549-1567 ◽  
Author(s):  
Václav Černý ◽  
Miloš Buděšínský ◽  
Miloš Ryba ◽  
František Tureček

Oxidation with 3-chloroperoxybenzoic acid of s-cis α,β-unsaturated ketones IX, XI and s-trans types X, XII was compared. The s-cis ketones show higher reactivity and furnish a higher yield of the corresponding α,β-epoxy ketones than the s-trans ketones. Products of the Baeyer-Villiger reaction are formed only in low yield. The dienone VI is oxidized predominantly to VII thus violating the rule that linear conjugated dienones are epoxidized at the double bond more distant from the carbonyl group; this result is in accord with the behaviour of s-cis α,β-unsaturated ketones. 1H NMR and 13C NMR data of the starting compounds and of the products are reported.


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