36917-44-9

Upstream product

• 108-75-8 2,4,6-trimethyl-pyridine 
• 3262-89-3 triphenylboroxine 
• 1309579-40-5 2,6-dimethyl-4-(2-methoxyethyl)pyridine 
• 100-44-7 benzyl chloride 

Relevant academic research and scientific papers

Ruthenium-catalyzed conversion of sp3 C-O bonds in ethers to C-C bonds using triarylboroxines

Catalytic conversion of unreactive sp3 C-O bonds in alkyl ethers to C-C bonds is described. Alkyl ethers bearing 2- or 4-pyridyl groups were coupled with triarylboroxines in the presence of a ruthenium catalyst. Triarylboroxines bearing a variety of functional groups including electron-withdrawing and -donating groups can be used for the reaction. No additional base was required for the coupling with the organoboron reagents, and base-sensitive groups can be tolerated. The reaction is considered to proceed via dehydroalkoxylation followed by addition of triarylboroxines to form C-C bonds.

Metal-chelating 2,6-disubstituted pyridine compounds and their use

Bifuncitonal chelating pyridine compound and its use for conferring chelating properties on organic compounds. The pyridine compound has the structure where (i) n is an integer 1 or 2, (ii) R1, R2 and R3 represent groups that have no electrons capable of significantly delocalizing or resonating with the pyridine ring, such as hydrogen, alkyl or aralkyl having an aliphatic carbon atom next to the pyridine ring; at least two of R1, R2 and R3 being hydrogen, iii) Z an Z' represent identical or different structures, each of which comprises at least one heteroatom having a free pair of electrons as that the said at least one heteroatom together with the nitrogen atom of the pyridine ring is capable of chelating a metal ion, iv) - - - - specifies that the group X-Y is a substituent replacing a hydrogen anywhere in the parent pyridine compound, and v) X-Y represents an organic group which is inert to said chelation, and in which iX is an inert and stable bridge and Y is a functional group or a residue of an organic compounbd that has properties conferred on the compound of formula II; said group X-Y being linked to the pyridine ring of formula II via an aliphatic carbon atom attached to and acid ester, salt and chelate forms thereof involving at least one of said chelating heteroatoms.

Metal-chelating 2,6-disubstituted pyridine compounds and their use

Bifunctional chelating pyridine compound and its use for conferring chelating properties on organic compounds. The pyridine compound has the structure where i) n is an integer 1 or 2, ii) R1, R2 and R3 represent groups that have no electrons capable of significantly delocalizing or resonating with the pyridine ring, such as hydrogen, alkyl or aralkyl having an aliphatic carbon atom next to the pyridine ring; at least two of R1, R2 and R3 being hydrogen, iii) Z and Z? represent identical or different structures, each of which comprises at least one heteroatom having a free pair of electrons so that the said at least one heteroatom together with the nitrogen atom of the pyridine ring is capable of chelating a metal ion, iv) ---- specifies that the group X-Y is a substituent replacing a hydrogen anywhere in the parent pyridine compound, and v) X-Y represents an organic group which is inert to said chelation, and in which X is an inert and stable bridge and Y is a functional group or a residue of an organic compound that has properties conferred on the compound of formula II; said group X-Y being linked to the pyridine ring of formula II via an aliphatic carbon atom attached to said ring,and acid ester, salt and chelate forms thereof involving at least one of said chelating heteroatoms.

PYRIDINES. XII - METALLATION REGIOSELECTIVE DE LA S-COLLIDINE : INFLUENCE DU SOLVANT ET DU CATION ASSOCIE SUR L'ISOMERISATION DES CARBANIONS FORMES. APPLICATION A LA BENZYLATION ET BENZOYLATION.

The metalation of s-collidine 1 by PhLi in Et2O, THF and DME leads to the kinetic anion (1a,S); in Et2O 1a is also the thermodynamic product.In THF and DME, (1a,S) isomerizes into the more delocalized thermodynamic anion (1b,S), without implication of a s

PYRIDINES. PARTIE IX - PLURIBENZYLATION DE LA S-COLLIDINE ET DE LA LUTIDINE-2,6

A literature survey of the polymetalation of 2,6-lutidine 2 shows different results about the site(s) of deprotonation and condensation with various electrophiles.This discrepancy prompts us to examine the polylithiation (PhLi 3 equivalents, Et2O) of s-collidine 1, 2,6-lutidine 2 and more briefly of 2,4-lutidine 3.Polylithiation takes place exclusively at the methyl groups of the same position vs the ring nitrogen : 2- and/or 6-methyl of 1.The previous regioselectivity observed in the case of the monometalation in Et2O is maintained.From 1 and 2, polylithiation gives picolyl anions which lead by reaction with PhCH2Cl, simultaneously to mono-, di-symmetrical, di-non-symmetrical α-derivatives, and tri- and tetra-symmetrical α,α'-compounds; but no product is formed from a benzylic β-anion.In the same way, the deprotonation of 2-methyl-6-(2-phenylethyl) pyridine 17 leads to 2,6-bis (2-phenylethyl) pyridine 19 and 2-methyl-6-dibenzylmethyl pyridine 18, to the exclusion of the β-compound 2-methyl-6-(2,3-diphenylpropyl) pyridine 21.The latter compound is formed in low yield, besides 19 and 18, in the conditions of the Tchitchibabine reaction (NaNH2, toluene).The structure of the benzylated compounds was established mainly from the 1H-nmr data.No product was isolated which would result from the nucleophilic attack of the generated carbanions at the pyridine carbons.