scholarly journals Modern Friedel-Crafts chemistry: Part 36. Facile synthesis of some new pyrido[3,2,1-jk]carbazoles via Friedel-Crafts cyclialkylations

2013 ◽  
Vol 78 (5) ◽  
pp. 611-619 ◽  
Author(s):  
Abd El-Aal ◽  
Ali Khalaf
Keyword(s):  
Grignard Reagent ◽  
Grignard Reagents ◽  
Facile Synthesis ◽  
Tertiary Alcohols

An efficient methodology for the synthesis of novel substituted pyrido[3,2,1-jk]carbazole via Friedel-Crafts cyclialkylations is reported. The methodology was realized by three-step protocol involved the addition of carbazole to 3-methylcrotononitrile. The resulted nitrile was hydrolyzed to desired ester, followed by addition of Grignard reagents to afford tertiary alcohols and/or reacted directly with different Grignard reagent to form the desired ketones. The later ketones were converted to both secondary and tertiary alcohols by reduction with LAH and addition of Grignard reagents respectively. These carbinols were cyclialkylated under Friedel-Crafts conditions catalyzed by AlCl3/CH3NO2, PTSA and PPA to give tri-and tetrasubstituted pyrido[3,2,1-jk]carbazole.

Facile synthesis of 4-substituted pyridines using grignard reagents

1982 ◽  
Vol 23 (38) ◽  
pp. 3935-3936 ◽  
Author(s):  
Kin-ya Akiba ◽  
Yuji Iseki ◽  
Makoto Wada
Keyword(s):  
Grignard Reagents ◽  
Facile Synthesis ◽  
Substituted Pyridines

The addition of organometallic reagents to tetramesityldigermene

2002 ◽  
Vol 80 (11) ◽  
pp. 1387-1392 ◽  
Author(s):  
Kyle L Fujdala ◽  
David W.K Gracey ◽  
Erica F Wong ◽  
Kim M Baines
Keyword(s):  
Ligand Exchange ◽  
Grignard Reagent ◽  
Thermal Conditions ◽  
Grignard Reagents ◽  
Ethylmagnesium Bromide ◽  
Organometallic Reagent ◽  
Organometallic Reagents ◽  
Thermal Cleavage

The thermolysis and photolysis of hexamesitylcyclotrigermane in the presence of ethylmagnesium bromide has been investigated. Under photochemical conditions, ethyldimesitylgermane, 1,2-diethyl-1,1,2-trimesityldigermane and ethyl-1,1,2,2-tetramesityldigermane were isolated and, under thermal conditions, 1,2,2-triethyl-1,1-dimesityl digermane and 2,2-diethyl-1,1,1-trimesityldigermane were isolated. The photolysis of hexamesitylcyclotrigermane in the presence of methyllithium has also been investigated. In both cases, the organometallic reagent adds to tetramesityl digermene and dimesitylgermylene formed by photochemical or thermal cleavage of the cyclotrigermane. In the case of the addition of the Grignard reagent, the resulting germyl Grignard reagent undergoes a facile ligand exchange reaction.Key words: digermene, germylene, Grignard reagents, alkyllithium reagents, germylmagnesium compounds, germyllithium compounds.

Grignard reagent formation via C-F bond activation: a centenary perspective

2022 ◽  
Author(s):  
Eunsung Lee ◽  
Ewa Pietrasiak
Keyword(s):  
Bond Dissociation Energy ◽  
Dissociation Energy ◽  
Grignard Reagent ◽  
Bond Activation ◽  
Grignard Reagents ◽  
Bond Dissociation ◽  
High Bond

Examples of Grignard reagents obtained by C-F bond activation with magnesium kept appearing in the literature over the last century. Due to the high bond dissociation energy of the C-F...

Diastereoselective Synthesis of Morpholine Derivatives from Grignard Reagents and N-Sulfinyl Imines

Synlett ◽  
2021 ◽  
Author(s):  
Eric P. A. Talbot ◽  
Joseph M. Bateman ◽  
Diana Chan ◽  
Mustafa Moroglu ◽  
Benjamin Rahemtulla
Keyword(s):  
Grignard Reagent ◽  
Stereoselective Synthesis ◽  
Grignard Reagents ◽  
Diastereoselective Synthesis ◽  
Step Process ◽  
Diastereoselective Addition ◽  
Morpholine Derivatives

The stereoselective synthesis of C3-substituted morpholine derivatives has been achieved through a two-step process involving diastereoselective addition of a Grignard reagent to a sulfinyl imine, followed by cyclization.

Use of Menthyl 2-Methoxynaphthalene-1-sulfinates in the Andersen Synthesis of Optically Active Sulfoxides. Facile Cleavage by Grignard Reagents of Some Aromatic Methyl Ethers

1994 ◽  
Vol 47 (10) ◽  
pp. 1925 ◽  
Author(s):  
KH Bell ◽  
LF Mccaffery
Keyword(s):  
Grignard Reagent ◽  
Methoxy Group ◽  
Optically Active ◽  
Grignard Reagents ◽  
Sulfinyl Group

The pure crystalline diastereomers (1R,2S,5R)-menthyl (R)- and (S)-2-methoxynaphthalene-1-sulfinate (1b) have been prepared and, by reaction with Grignard reagents (the Andersen procedure), converted into optically active alkyl and aryl 2-methoxynaphthyl sulfoxides in 67-77% yields. Use of an excess of Grignard reagent results in facile O-alkyl cleavage of the methoxy group to the corresponding naphthol or a competing loss of the alkyl- or aryl- sulfinyl group to form 2-methoxynaphthalene. Pure diastereomers of menthyl 2,7- dimethoxynaphthalene-1-sulfinate (2b) and menthyl 4-methoxynaphthalene-1-sulfinate (3b) have also been prepared and their reactions with Grignard reagents have been studied.

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