27248-04-0

Basic information

• Product Name: Pyridine, 4-[(trimethylsilyl)oxy]-
• CAS NO: 27248-04-0
• Molecular Formula: C8H13NOSi
• Molecular Weight: 167.283
• Mol File: 27248-04-0.mol

Chemical Properties

• CAS DataBase Reference: Pyridine, 4-[(trimethylsilyl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 4-[(trimethylsilyl)oxy]-(27248-04-0)
• EPA Substance Registry System: Pyridine, 4-[(trimethylsilyl)oxy]-(27248-04-0)

Safety Data

• Hazardous Substances Data: 27248-04-0(Hazardous Substances Data)

Upstream product

• 131061-36-4 methylsilyl trifluoromethanesulfonate 
• 332940-69-9 tert-butyl 4-oxopyridine-1-carboxylate 
• 75-77-4 chloro-trimethyl-silane 
• 108-96-3 4-pyridone 

Downstream Products

• 71492-26-7 (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-3-(4-oxo-4H-pyridin-1-ylmethyl)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid benzhydryl ester 
• 18342-24-0 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4(1H)-pyridinone 
• 2456-81-7 4-pyrrolidin-1-ylpyridine 
• 131580-98-8 p-Methoxybenzyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-(1-diphenylmethoxycarbonyl-1-methyl)ethoxyiminoacetamido>-3-(4-pyridon-1-yl)methyl-3-cephem-4-carboxylate 
• 72359-37-6 1-benzylpyridin-4(1H)-one 
• 93580-01-9 1-benzhydryl-1H-pyridin-4-one 
• 71492-30-3 (6R)-7t-((Ξ)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-3-(4-oxo-4H-pyridin-1-ylmethyl)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 71492-28-9 (6R)-7t-((Ξ)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-5ξ,8-dioxo-3-(4-oxo-4H-pyridin-1-ylmethyl)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 93580-04-2 1-Benzhydryl-2,3-dihydro-1H-pyridin-4-one 
• 35488-00-7 1-methyl-2,3-dihydro-4-pyridone 
• 35487-98-0 2,3-dihydro-1-(phenylmethyl)-4(1H)-pyridinone 
• 116211-45-1 1-(2-Hydroxy-2,2-diphenyl-ethyl)-1H-pyridin-4-one 
• 116211-47-3 1-[2-(4-Chloro-phenyl)-2-hydroxy-ethyl]-1H-pyridin-4-one 
• 116211-46-2 1-[2-(4-Chloro-phenyl)-2-hydroxy-propyl]-1H-pyridin-4-one 

Relevant articles and documents

Conjugate addition reactions of N -carbamoyl-4-pyridones and 2,3-dihydropyridones with grignard reagents in the absence of Cu(I) Salts

N-Boc- and N-ethoxycarbonyl-4-pyridones and the resulting 2,3-dihydropyridones undergo 1,4-addition reactions with Grignard reagents in the presence of chlorotrimethylsilane (TMSCl) or BF3·Et 2O in excellent yields. Copper catalysis is not required, and mechanistic considerations suggest that the reaction is proceeding by a conjugate addition pathway rather than by a pathway involving 1,2-addition to an intermediate pyridinium ion. TMSCl-mediated conjugate addition of Grignard reagents to 2-substituted-2,3-dihydropyridones gives the trans-2,6-disubstitued piperidinones stereoselectively, while cuprate reagents give either the trans or cis diastereomers or mixtures.

Preparation of Didehydropyridines from (Trimethylsilyl)pyridines

Halogen-substituted (trimethylsilyl)pyridines 2, 3, 5-7 and trifluoromethylsulfonyloxy-substituted (trimethylsilyl)pyridines 9b, 11b are obtained from 2- and 3-halopyridines 1, 4 or hydroxypyridines 8, 10, and 12.Reactions of the 3- and 2-(trimethylsilyl)pyridines 2, 9b and 11b with bases in the presence of furans 15 give only protodesilylation or hydrolysis products but no indication is found for the formation of a 2,3-didehydropyridine. 3-Bromo-4-(trimethylsilyl)pyridine (5a) reacts with KOCMe3 in the presence of furan (15a) to give a mixture of products from which the isoquinoline derivative 20 and the tert-butoxypyridines 23, 24 are formed by addition to 3,4-didehydropyridine.Under comparable conditions far higher yields of 3,4-didehydropyridines are obtained by treatment of the 3-halo-2,4-bis(trimethylsilyl)pyridines 7 with strong bases. Key Words: Didehydropyridines, synthesis of