Flavan derivatives. XXXI. Reduction products from Isochromeno(4',3':2,3)-chromones

1971 ◽  
Vol 24 (3) ◽  
pp. 563 ◽  
Author(s):  
JW Clark-Lewis ◽  
MM Mahandru
Keyword(s):  
Catalytic Hydrogenation ◽  
Lithium Aluminium Hydride ◽  
Aryl Group ◽  
Methoxy Derivative ◽  
Lithium Aluminium

Some reduction products (chromens, chroman-4-ols, and flavonols) obtained from isochromeno(4?,3?:2,3)chromone and its 7-methoxy derivative with lithium aluminium hydride, sodium di(2- methoxyethoxy)aluminium hydride, and catalytic hydrogenation are described. Allylic coupling is evident in isochromano(4?,3?:2,3)- chrom-3-ens, and the absence of allylic coupling in 3-alkoxyflav-3-enes is therefore attributed to the latter occurring in the conformation with the 2-aryl group axial (cf.1).

Reactions of propargyl alcohols. VI. Lithium aluminium hydride reductions of 2,2-Dimethyl-3-phenylhex-4-yn-3-ol, its 1-methoxy derivative and 2,2-Di-(methoxymethyl)-3-phenylhex-4-yn-3-ol

1983 ◽  
Vol 36 (3) ◽  
pp. 581
Author(s):  
JW Blunt ◽  
MP Hartshorn ◽  
MHG Munro ◽  
T Lee ◽  
RS Thompson ◽  
...  
Keyword(s):  
Lithium Aluminium Hydride ◽  
Methoxy Derivative ◽  
Lithium Aluminium ◽  
Solvent Dependence ◽  
Propargyl Alcohols

Lithium aluminium hydride reductions of 2,2-dimethyl-3-phenyIhex-4-yn-3-ol (5a) and its methoxy (5b) and dimethoxy (5c) derivatives are reported. The nature of the solvent dependence of these reactions is identified, and the mode of formation of the products of the reactions determined.

Bicyclo[2.2.2]octane-2-spirocyclohexanes, Part 2[1]. Reduction Products of Spirodiisophora-3′,6-dione

1991 ◽  
Vol 46 (11) ◽  
pp. 1557-1567 ◽  
Author(s):  
Frederick Kurzer ◽  
Zakir Kapadia
Keyword(s):  
Catalytic Hydrogenation ◽  
Nmr Spectra ◽  
Cyclohexane Ring ◽  
Lithium Aluminium Hydride ◽  
Lithium Aluminium ◽  
Functional Derivatives ◽  
The Individual ◽  
C Nmr

The reduction of spirodiisophora-3′,6-dione under various conditions occurs exclusively at its 3′-keto-function in the cyclohexane ring. The action of lithium aluminium hydride yields the 3′-eq-hydroxyketone, while catalytic hydrogenation, hydroboration and the action of metal borohydride produces the 3′-ax-epimer. The conformers give rise to pairs of distinct epimeric functional derivatives. Anhydrous hydrazine removes the 3′-oxygen function of the 3′,6-dione entirely, with formation of spirodiisophor-6-one. Catalytic hydrogenation of the 3′-oximino-6-ketone yields the corresponding 3′-amine. The 13C NMR spectra of the individual products are assigned and correlated with their structures.

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).

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