86801-40-3

Upstream product

• 110-86-1 pyridine 
• 1885-14-9 phenyl chloroformate 

Downstream Products

• 188824-71-7 4-(2-Fluoro-phenyl)-4H-pyridine-1-carboxylic acid phenyl ester 
• 188824-70-6 4-(2-Methoxy-phenyl)-4H-pyridine-1-carboxylic acid phenyl ester 
• 188824-72-8 4-(4-Diallylamino-phenyl)-4H-pyridine-1-carboxylic acid phenyl ester 
• 110601-02-0 4-Isopropyl-4H-pyridine-1-carboxylic acid phenyl ester 
• 87672-89-7 4-Cyclohexyl-4H-pyridine-1-carboxylic acid diethylamide 
• 110601-00-8 4-Cyclohexyl-4H-pyridine-1-carboxylic acid phenyl ester 
• 313070-89-2 1-(phenoxycarbonyl)-2-(2-propenyl)-1,2-dihydropyridine 
• 87673-00-5 3-acetyl-4-phenylpyridine 
• 87672-96-6 4-Cyclohexyl-3-acetylpyridine 
• 87672-97-7 4-Cyclohexyl-3-propionylpyridine 
• 87672-98-8 4-Cyclohexyl-3-butyrylpyridine 
• 87672-99-9 4-Cyclohexyl-3-isobutyrylpyridine 

Relevant academic research and scientific papers

A highly regioselective indium-mediated allylation of pyridine derivatives: Synthesis of (±)-dihydropinidine from pyridine

The preparation of various 1-acyl-1,2-dihydropyridines with high regioselectivity by indium-mediated allylation of the corresponding 1-acylpyridinium salts is demonstrated. This is applied to the synthesis of (±)-dihydropinidines. (C) 2000 Elsevier Science Ltd.

Regioselective reaction of 2-indolylcyanocuprates with electrophiles

The reaction of 2-indolylcyanocuprate with electrophiles was found to give rise to 2- and 3-substituted indoles in regioselective manner.

Kinetics and mechanism of the pyridinolysis of phenyl chloroformates in acetonitrile

Kinetic studies on the reactions of Y-phenyl chloroformates with X- pyridines in acetonitrile are carried out at 25.0 °C. Both the Hammett and Bronsted plots are linear with enhanced substituent constants, σ(p)-, and basicities, pK(a)-, for strong para π-acceptor X-substituents, p-CN and p- CH3CO. This indicates that the electron-rich formate (O-C-O) moiety overlaps with the pyridine ring π-system enabling, through conjugation with the para π-acceptors, the rate-limiting formation of a tetrahedral intermediate. The difference in the aminolysis mechanism between methyl, II, and phenyl chloroformate, III, is attributed to the much stronger electron-donating polarizability effect of C6H5 than of CH3. The proposed mechanism is supported by a relatively small β(X) (? 0.3) and by the lower δH(+) (6.7 kcal mol-1) and δS(+) (-44 eu) values for a stronger donor Y (Y = p- CH3O) coupled with a stronger para π-acceptor (X = p-CN) in pyridine.

Versatile Synthesis of Dihydroquinolines and Quinoline Quinones Using Cyclobutenediones. Construction of the Pyridoacridine Ring System

1-BOC-2-lithio-1, 4-dihydropyridines were condensed with 3,4-disubstituted cyclobutenediones to produce 1,2-adducts. Neat thermolysis under oxygen-free conditions produced substituted 1,4-dihydroquinoline hydroquinones in which the tert-butoxy residue of the BOC group was displaced by a phenolic residue, generating an oxazolone ring that functioned to protect both rings of the dihydroquinoline hydroquinone from untimely oxidation. Oxidative aromatization with concomitant loss of the oxazolone ring was achieved using 2 equiv of o-chloranil in acetic acid and provided substituted quinoline quinones in good yields. By use of this strategy, a concise synthesis of the pyridoacridine ring system was achieved.

REACTIONS OF TRIETHYL(1-METHYL-2-INDOLYL)BORATE WITH N-CARBOPHENOXYPYRIDINIUM DERIVATIVES

The reaction of triethyl(1-methyl-2-indolyl)borate with several N-carbophenoxypyridinium derivatives afforded 3-substituted 2-ethyl-1-methylindoles in the absence of copper(I) ion, while 3-substituted 1-methylindoles were obtained in the presence of coppe