Chemical transformations of ethyl 3,5-dicyano-2,4,4,6-tetramethyl-1,4-dihydro-1-pyridyl acetate, sythesis of a new N-vinyl monomer

1983 ◽  
Vol 48 (2) ◽  
pp. 617-622 ◽  
Author(s):  
Jaroslav Paleček ◽  
Manfred Pavlík ◽  
Josef Kuthan
Keyword(s):  
Carboxylic Acid ◽  
Electron Impact ◽  
Title Compound ◽  
Vinyl Monomer ◽  
Molecular Spectra ◽  
Chemical Transformations ◽  
Lithium Aluminium Hydride ◽  
Lithium Aluminium ◽  
Functional Transformations

Ethoxycarbonyl group in the title compound I undergoes regioselective functional transformations to give the amide II and the carboxylic acid III. Reduction with lithium aluminium hydride gave the alcohol V whose p-toluenesulfonate was converted directly or via 2-iodoethyl derivative VIII into the N-vinyl monomer IX. Absorption molecular spectra of the synthesized compounds I-IX, as well as their fragmentation by electron impact, are discussed.

Lithium aluminium hydride-aluminium chloride reduction of steroidal cyclic acetals

1971 ◽  
Vol 24 (1) ◽  
pp. 143 ◽  
Author(s):  
MS Ahmad ◽  
SC Logani
Keyword(s):  
Spectral Properties ◽  
Aluminium Chloride ◽  
Chemical Transformations ◽  
Lithium Aluminium Hydride ◽  
Glycol Ethers ◽  
Cyclic Acetals ◽  
Lithium Aluminium

Lithium aluminium hydride-aluminium chloride (1 : 1, AlH2Cl) reduction of 3,3-ethylenedioxycholest-5-ene (5), 3,3-ethylenedioxy-5α-oholestane (7), 6,6-ethyl-enedioxy-5α-cholestane (7), and 3,3-(1?- methylethylenedioxy)cholest-5-en (8a), gave the glycol ethers (9), (17), (21a), and (24), respectively. The structures of the ethers (9), (17), (21a), and (24) have been established by their spectral properties and chemical transformations. A mechanism of the hydrogenolysis is presented.

Beiträge zur Chemie des Phosphors, 126. Tris(tert-butylphosphino)-phosphan, P(t-BuPH)3 - ein teilsubstituiertes Derivat von iso-P4H6/ Contributions to the Chemistry of Phosphorus, 126. Tris(tert - butylphosphino)phosphane, P(t-BuPH)3 - a Partially Substituted Derivative of iso-P4H6

1983 ◽  
Vol 38 (5) ◽  
pp. 537-542 ◽  
Author(s):  
Marianne Baudler ◽  
Jochen Hellmann ◽  
Thomas Schmidt
Keyword(s):  
Title Compound ◽  
Pure State ◽  
Lithium Aluminium Hydride ◽  
Nmr Parameters ◽  
Lithium Aluminium ◽  
State 1

AbstractThe reaction of tris(bromo-tert-butylphosphino)phosphane, P(t-BuPBr)3, with lithium aluminium hydride leads to the title compound P(t-BuPH)3 (1), which could be isolated in a pure state. 1 is the first partially substituted derivative of iso-tetraphosphane(6), P(PH2)3, and was characterized in all details. Because of the chirality of the Z-BuPHgroups, 1 forms two diastereomers with RRS(SSR)- and RRR(SSS)-configuration in a ratio of about 3:1. The conformation of both isomers, which could be deduced from the 31P NMR parameters, is mainly determined by the steric situation of the molecule.

Fluorinated tricyclic neuroleptics: Synthesis and pharmacology of 2-chloro-8-fluoro-4-(4-methylpiperazino)-4,5-dihydrothieno[2,3-b]-1-benzothiepin

1981 ◽  
Vol 46 (9) ◽  
pp. 2222-2233 ◽  
Author(s):  
Zdeněk Polívka ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Title Compound ◽  
Substitution Reaction ◽  
Phosphorus Pentoxide ◽  
Lithium Aluminium Hydride ◽  
Lithium Aluminium ◽  
Chloro Derivative ◽  
Neuroleptic Agent ◽  
Long Acting ◽  
Animal Tests

Diazotization of 4-fluoroanthranilic acid (V) and the following reaction with sodium disulfide gave the dithio diacid VII which was reduced with lithium aluminium hydride to 4-fluoro-2-mercaprobenzyl alcohol (XI). Its reaction with 2-chloro-5-iodothiophene afforded the alcohol XIII which was transformed via the chloride XIV and the nitrile XV to [2-(5-chloro-2-thienylthio)-4-fluorophenyl]acetic acid (XVI). Cyclization with phosphorus pentoxide in toluene resulted in 2-chloro-8-fluorothieno[2,3-b]-1-benzothiepin-4(5H)-one (XVIII) which was converted via the alcohol XIX to the chloro derivative XX. The substitution reaction with 1-methylpiperazine led to the title compound IV which is a long-acting and very potent tranquillizer but did not reveal, in the animal tests performed, the properties of a neuroleptic agent.

The saturated pyrrolizidine diols. III. A partial synthesis of turneforcidine

1969 ◽  
Vol 22 (12) ◽  
pp. 2657 ◽  
Author(s):  
AJ Aasen ◽  
CCJ Culvenor
Keyword(s):  
Carboxylic Acid ◽  
Lithium Aluminium Hydride ◽  
Partial Synthesis ◽  
Lithium Aluminium ◽  
Stepwise Reduction

Turneforcidine has been prepared by the oxidation of methyl 7α-hydroxy- 8α-pyrrolizidine-1α-carboxylate to the 7-keto compound and stepwise reduction with hydrogen/platinum and lithium aluminium hydride. 7β- Hydroxy-8α-pyrrolizidine-1β-carboxylic acid is not epimerized by alkali but converted into the stable γ-lactone (VI).

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

3-(s-Hydrindacen-4-yl)propylamines and 4-(s-hydrindacen-4-yl)butylamines; Synthesis and pharmacological screening

1981 ◽  
Vol 46 (8) ◽  
pp. 1800-1807 ◽  
Author(s):  
Zdeněk Vejdělek ◽  
Marie Bartošová ◽  
Miroslav Protiva
Keyword(s):  
Malonic Acid ◽  
Local Anaesthetics ◽  
Lithium Aluminium Hydride ◽  
Spasmolytic Activity ◽  
Lithium Aluminium ◽  
Malonic Acid Derivatives ◽  
Pharmacological Screening ◽  
Hydroxyethyl Piperazine

4-Chloromethyl-s-hydrindacene (VIIa) was transformed via the malonic acid derivatives VIIIa and IXa to the acid Xb which afforded in four steps the homological acid Xc. Reactions of chlorides of both acids (XIbc ) with dimethylamine, 1-methylpiperazine and 1-(2-hydroxyethyl)piperazine led to the amides XIIbc-XIVbc which were reduced with lithium aluminium hydride to the title compounds IVcd-VIcd. The amines obtained show central neuroleptic effects only in subtoxic doses; they are also potent local anaesthetics and have significant spasmolytic activity of the neurotropic as well as musculotropic type.

Substituted N,N-Dimethyl-3-(phenylthio)- and -4-(phenylthio)benzylamines

1992 ◽  
Vol 57 (1) ◽  
pp. 194-203 ◽  
Author(s):  
Karel Šindelář ◽  
Vojtěch Kmoníček ◽  
Marta Hrubantová ◽  
Zdeněk Polívka
Keyword(s):  
Serotonin Receptors ◽  
Hydrobromic Acid ◽  
Antidepressant Activity ◽  
Benzoic Acids ◽  
Lithium Aluminium Hydride ◽  
Acid Chlorides ◽  
Activity Inhibition ◽  
Lithium Aluminium ◽  
The Brain

(Arylthio)benzoic acids IIa - IIe and VIb - VId were transformed via the acid chlorides to the N,N-dimethylamides which were reduced either with diborane "in situ" or with lithium aluminium hydride to N,N-dimethyl-(arylthio)benzylamines Ia - Ie and Vb - Vd. Leuckart reaction of the aldehydes IX and X with dimethylformamide and formic acid afforded directly the amines Va and Ve. Demethylation of the methoxy compounds Ia and Ve with hydrobromic acid resulted in the phenolic amines If and Vf. The most interesting N,N-dimethyl-4-(phenylthio)benzylamine (Va) hydrochloride showed affinity to cholinergic and 5-HT2 serotonin receptors in the rat brain and some properties considered indicative of antidepressant activity (inhibition of serotonin re-uptake in the brain and potentiation of yohimbine toxicity in mice).

Synthesis of 3-(6-Azauracil-5-yl)anthranilic Acid and Its Application to the Preparation of Other 1,2,4-Triazine Derivatives

1996 ◽  
Vol 61 (6) ◽  
pp. 941-945 ◽  
Author(s):  
Jan Hlaváč ◽  
Jan Slouka
Keyword(s):  
Carboxylic Acid ◽  
Anthranilic Acid ◽  
Title Compound ◽  
Triazine Derivatives

The title compound was synthesized by alkaline recyclization of isatin-7-carboxylic acid semicarbazone and used for the preparation of 3-oxo-2,3-dihydro-5H-1,2,4-triazino[5,6-b]indol-6-carboxylic acid (8) and 3-oxo-2,3,4,6-tetrahydro-1,2,4-triazino[5,6-c]cinnoline-7-carboxylic acid (9).

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