Substitution Reactions and Meso Derivatives of 1,2-Benzanthracene

1938 ◽  
Vol 60 (8) ◽  
pp. 1893-1896 ◽  
Author(s):  
Louis F. Fieser ◽  
E. B. Hershberg
Keyword(s):  
Substitution Reactions ◽  
Derivatives Of

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

Rates of substitution reactions of some derivatives of hexacarbonylmolybdenum(0)

1967 ◽  
Vol 7 (3) ◽  
pp. 461-471 ◽  
Author(s):  
Franco Zingales ◽  
Franco Canziani ◽  
Fred Basolo
Keyword(s):  
Substitution Reactions ◽  
Derivatives Of

scholarly journals Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications

2014 ◽  
Vol 10 ◽  
pp. 1919-1932 ◽  
Author(s):  
Mahesh K Lakshman ◽  
Manish K Singh ◽  
Mukesh Kumar ◽  
Raghu Ram Chamala ◽  
Vijayender R Yedulla ◽  
...  
Keyword(s):  
Amide Bond ◽  
Coupling Agents ◽  
Cyclic Ketones ◽  
Substitution Reactions ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Peptide Coupling ◽  
Acyclic Nucleoside ◽  
Derivatives Of

(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4-methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads to 1-alkoxy-1H-benzo- (Bt-OR) and 7-azabenzotriazoles (At-OR). Although BOP undergoes reactions with alcohols to furnish 1-alkoxy-1H-benzotriazoles, Bt-OTs proved to be superior. Both, primary and secondary alcohols undergo reaction under generally mild reaction conditions. Correspondingly, 1-alkoxy-1H-7-azabenzotriazoles were synthesized from At-OTs. Mechanistically, there are three pathways by which these peptide-coupling agents can react with alcohols. From 31P{1H}, [18O]-labeling, and other chemical experiments, phosphonium and tosylate derivatives of alcohols seem to be intermediates. These then react with BtO− and AtO− produced in situ. In order to demonstrate broader utility, this novel reaction has been used to prepare a series of acyclic nucleoside-like compounds. Because BtO− is a nucleofuge, several Bt-OCH2Ar substrates have been evaluated in nucleophilic substitution reactions. Finally, the possible formation of Pd π–allyl complexes by departure of BtO− has been queried. Thus, alpha-allylation of three cyclic ketones was evaluated with 1-(cinnamyloxy)-1H-benzo[d][1,2,3]triazole, via in situ formation of pyrrolidine enamines and Pd catalysis.

Derivatives of eis-NPCl2(NSOCl)2 and (NPCl2)2NSOCl, Part IX [1] Substitution Reactions of cis-NPCl2(NSOCl)2 with Piperidine

1978 ◽  
Vol 33 (9) ◽  
pp. 959-963 ◽  
Author(s):  
H. H. Baalmann ◽  
R. Keizer ◽  
J. C. van de Grampel ◽  
C. Kruk
Keyword(s):  
Room Temperature ◽  
Substitution Reactions ◽  
Substitution Pattern ◽  
Nmr Data ◽  
Data Application ◽  
Structure Assignment ◽  
Derivatives Of ◽  
C Nmr

Aminolysis of cis-NPCl2(NSOCl)2 by piperidine in acetonitrile at room temperature proceeds via a non-geminal substitution pattern. During the first substitution step the reactivity of a SOCl-centre appears to be greater than that of a PCl2-centre. The second and third substitution step successively take place at the PCl2- and remaining SOCl-centre. The different isomeric forms of the mono-, bis-, tris-, and tetrakis(piperidino) derivatives are characterized by means of 31P NMR data. Application of 13C NMR leads in two cases to a structure assignment.

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