2- And 3-fluoro derivatives of clorotepin and related compounds; 6- And 7-fluoro derivative of chlorprothixene

1975 ◽  
Vol 40 (3) ◽  
pp. 719-737 ◽  
Author(s):  
M. Rajšner ◽  
J. Metyšová ◽  
E. Svátek ◽  
F. Mikšík ◽  
M. Protiva
Keyword(s):  
Fluoro Derivative ◽  
Derivatives Of ◽  
Related Compounds ◽  
Fluoro Derivatives

Fluorinated neuroleptics of the 10-piperazino-10,11-dihydrodibenzo[b,f]thiepin series; 6-Fluoro derivatives of perathiepin, octoclothepin, doclothepin and some related compounds

1979 ◽  
Vol 44 (7) ◽  
pp. 2139-2155 ◽  
Author(s):  
Irena Červená ◽  
Jiřina Metyšová ◽  
Václav Bártl ◽  
Miroslav Protiva
Keyword(s):  
Metabolic Pathway ◽  
Pharmacological Profile ◽  
Fluoro Derivative ◽  
Sedative Effects ◽  
Neuroleptic Agent ◽  
A Minor ◽  
Derivatives Of ◽  
Related Compounds ◽  
Fluoro Derivatives ◽  
Central Depressant

The synthesis of a series of 6-fluoro-10-piperazino-10,11-dihydrodibenzo[b,f]thiepins Ic-IIIc, Vc and VIc is described; these compounds are derivatives of the neuroleptic agents perathiepin (Ia), octoclothepin (IIIa), doclothepin (Va) and their hydroxyethyl analogues IIa and VIa in which the metabolic hydroxylation to position 6 was made impossible by blockade. The synthesis used common procedures via the intermediates VII-XVIII. Fluorination in position 6 does not influence much the pharmacological profile of the compounds indicating that hydroxylation in position 6 is only a minor metabolic pathway. The most interesting substance is the 6-fluoro derivative of octoclothepin (IIIc) which is a potent central depressant and neuroleptic agent with some protraction of the sedative effects.

Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion

2005 ◽  
Vol 70 (12) ◽  
pp. 2075-2085 ◽  
Author(s):  
Jiří Kroutil ◽  
Klára Jeništová
Keyword(s):  
Fluoride Anion ◽  
Ring Cleavage ◽  
Protecting Group ◽  
Reaction Conditions ◽  
Aziridine Ring ◽  
Cleavage Reactions ◽  
Derivatives Of ◽  
Fluoro Derivatives

Aziridine ring cleavage reactions of five N-nosylepimines (2-6) having D-talo, D-galacto, D-manno, and D-allo configurations with potassium hydrogendifluoride under various reaction conditions have been performed. The cleavage regioselectively afforded diaxial isomers of vicinal amino-fluoro derivatives of 1,6-anhydro-β-D-gluco- and mannopyranose 7-11 in 51-94% yields. Removal of 2-nitrobenzenesulfonyl protecting group with benzenethiol has been attempted in the case of compound 10.

Synthesis of 5,7-dihydroxynaphthoquinone derivatives and their reactions with nucleophiles: Nitration of 2,3-dimethylnaphthalene and subsequent transformations

1976 ◽  
Vol 29 (10) ◽  
pp. 2247 ◽  
Author(s):  
HJ Banks ◽  
DW Cameron ◽  
MJ Crossley ◽  
EL Samuel
Keyword(s):  
Unusual Reaction ◽  
Nitro Derivatives ◽  
Reactions With Nucleophiles ◽  
Derivatives Of ◽  
Related Compounds ◽  
Benzenoid Ring

5,7-Dihydroxy-2,3-dimethyl-l,4-naphthoquinone (5) and related compounds have been synthesized. The quinone affords an accessible substrate for studying an unusual reaction with nucleophiles, which involves attack at the 8-position, i.e. at the benzenoid ring. An unsuccessful approach to (5) has led to tri- and tetra-nitro derivatives of 2,3-dimethylnaphthalene. Reduction of the former and subsequent conversions have given aminonaphthoquinone and perimidinone derivatives.

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