Sulfonation of strychnine and some related compounds by sulfur dioxide – manganese dioxide (the Leuchs reaction)

1980 ◽  
Vol 58 (22) ◽  
pp. 2380-2385 ◽  
Author(s):  
John T. Edward ◽  
Patrick G. Farrell ◽  
Syed A. Samad ◽  
Richard Wojtowski ◽  
Sin Cheong Wong
Keyword(s):  
Sulfur Dioxide ◽  
Manganese Dioxide ◽  
Quaternary Salts ◽  
Related Compounds ◽  
C Nmr

On the basis of pK measurements, 13C nmr, and chemical arguments, the zwitterionic structures 3 and 4 have been assigned to the two minor products obtained by sulfonating strychnine or brucine in water with a mixture of sulfur dioxide and manganese dioxide. The same reagent sulfonates the quaternary salts of strychnine and brucine to give betaines, but fails to sulfonate many other strychnine derivatives as well as a number of other alkaloids examined.

ChemInform Abstract: SULFONATION OF STRYCHNINE AND SOME RELATED COMPOUNDS BY SULFUR DIOXIDE-MANGANESE DIOXIDE (THE LEUCHS REACTION)

1981 ◽  
Vol 12 (14) ◽  
Author(s):  
J. T. EDWARD ◽  
P. G. FARRELL ◽  
S. A. SAMAD ◽  
R. WOJTOWSKI ◽  
S. C. WONG
Keyword(s):  
Sulfur Dioxide ◽  
Manganese Dioxide ◽  
Related Compounds

Synthesis and Structure Assignment of 2-(4-Methoxybenzyl)cyclohexyl β-D-Glucopyranoside Enantiomers

2006 ◽  
Vol 71 (10) ◽  
pp. 1470-1483 ◽  
Author(s):  
David Šaman ◽  
Pavel Kratina ◽  
Jitka Moravcová ◽  
Martina Wimmerová ◽  
Zdeněk Wimmer
Keyword(s):  
Analytical Data ◽  
Chiral Hplc ◽  
Nmr Analysis ◽  
Target Structure ◽  
Enantiomerically Pure ◽  
Whole Cells ◽  
H Nmr ◽  
Structure Assignment ◽  
Related Compounds ◽  
C Nmr

Glucosylation of the cis- and trans-isomers of 2-(4-methoxybenzyl)cyclohexan-1-ol (1a/1b, 2a/2b, 1a or 2a) was performed to prepare the corresponding alkyl β-D-glucopyranosides, mainly to get analytical data of pure enantiomers of the glucosides (3a-6b), required for subsequent investigations of related compounds with biological activity. One of the employed modifications of the Koenigs-Knorr synthesis resulted in achieving 85-95% yields of pure β-anomers 3a/3b, 4a/4b, 3a or 4a of protected intermediates, with several promoters and toluene as solvent, yielding finally the deprotected products 5a/5b, 6a/6b, 5a or 6a as pure β-anomers. To obtain enantiomerically pure β-anomers of the target structure (3a, 4a, 5a and 6a) for unambiguous structure assignment, an enzymic reduction of 2-(4-methoxybenzyl)cyclohexan-1-one by Saccharomyces cerevisiae whole cells was performed to get (1S,2S)- and (1S,2R)-enantiomers (1a and 2a) of 2-(4-methoxybenzyl)cyclohexan-1-ol. The opposite enantiomers of alkyl β-D-glucopyranosides (5b and 6b) were obtained by separation of the diastereoisomeric mixtures 5a/5b and 6a/6b by chiral HPLC. All stereoisomers of the products (3a-6b) were subjected to a detailed 1H NMR and 13C NMR analysis.

NMR-spektroskopische Untersuchungen an 1,1-Thiophendioxid und verwandten Verbindungen / NMR Spectroscopical Investigations of Thiophene 1,1-Dioxide and Related Compounds

1984 ◽  
Vol 39 (7) ◽  
pp. 915-920 ◽  
Author(s):  
Herbert Meier ◽  
Thomas Molz ◽  
Heinz Kolshorn
Keyword(s):  
Computer Simulation ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Multiple Resonance ◽  
Nmr Data ◽  
Cyclic Diene ◽  
Related Compounds ◽  
C Nmr

The 1H and 13C NMR data of thiophene 1,1-dioxide (3) and related compounds, especially of the precursor 2 and the consecutive product 5 are evaluated by computer simulation and multiple resonance. Chemical shifts and coupling constants reveal that 3 has the character of a cyclic diene. Diatropic or paratropic effects can be excluded.

Oxidative dimerisations of natural rethrolones and related compounds with manganese dioxide

1971 ◽  
pp. 9 ◽  
Author(s):  
L. Crombie ◽  
J. A. Ellis ◽  
R. Gould ◽  
Gerald Pattenden ◽  
M. Elliott ◽  
...  
Keyword(s):  
Manganese Dioxide ◽  
Related Compounds

Solution Structures of Pyrophthalones, I Structure and Conformation of 1,3-Indandionato-2(2-pyridinium)-betaïn — a 1H/13C NMR Approach

1987 ◽  
Vol 42 (1) ◽  
pp. 31-36 ◽  
Author(s):  
Erhard T. K. Haupt ◽  
Heindirk tom Dieck ◽  
Panayot R. Bontchev
Keyword(s):  
Hydrogen Bond ◽  
Intramolecular Hydrogen Bond ◽  
13C Nmr ◽  
Nmr Spectra ◽  
Complete Analysis ◽  
Solution Structures ◽  
The Stability ◽  
Intramolecular Hydrogen ◽  
Related Compounds ◽  
C Nmr

AbstractThe complete analysis of the 1H/13 C NMR spectra of α-Pyrophthalone and related compounds demonstrates that the earlier static planar description of the molecules is invalid for polar sol-vents, and here the stability of any intramolecular hydrogen bond is small.

scholarly journals Synthesis of compounds related to the anti-migraine drug eletriptan hydrobromide

2012 ◽  
Vol 8 ◽  
pp. 1400-1405 ◽  
Author(s):  
Suri Babu Madasu ◽  
Nagaji Ambabhai Vekariya ◽  
M N V D Hari Kiran ◽  
Badarinadh Gupta ◽  
Aminul Islam ◽  
...  
Keyword(s):  
Mass Spectroscopy ◽  
Acute Treatment ◽  
Selective Serotonin ◽  
Spectroscopic Techniques ◽  
Active Pharmaceutical Ingredients ◽  
Pharmaceutical Ingredients ◽  
H Nmr ◽  
Related Compounds ◽  
C Nmr ◽  
Anti Migraine Drug

Eletriptan hydrobromide (1) is a selective serotonin (5-HT1) agonist, used for the acute treatment of the headache phase of migraine attacks. During the manufacture of eletriptan hydrobromide the formation of various impurities were observed and identified by LC–MS. To control the formation of these impurities during the preparation of active pharmaceutical ingredients, the structure of the impurities must be known. Major impurities of the eletriptan hydrobromide synthesis were prepared and characterized by using various spectroscopic techniques, i.e., mass spectroscopy, FTIR , 1H NMR, 13C NMR/DEPT, and further confirmed by co-injection in HPLC. The present study will be of great help in the synthesis of highly pure eletriptan hydrobromide related compounds.

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