74632-03-4

Basic information

• Product Name: Diethyl 4-oxo-1,4-dihydro-3,5-pyridinedicarboxylate
• Synonyms: Diethyl 4-oxo-1,4-dihydro-3,5-pyridinedicarboxylate;diethyl 4-oxo-1,4-dihydropyridine-3,5-dicarboxylate;diethyl 4-hydroxypyridine-3,5-dicarboxylate
• CAS NO: 74632-03-4
• Molecular Formula: C₁₁H₁₃NO₅
• Molecular Weight: 239.226
• Mol File: 74632-03-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Diethyl 4-oxo-1,4-dihydro-3,5-pyridinedicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 4-oxo-1,4-dihydro-3,5-pyridinedicarboxylate(74632-03-4)
• EPA Substance Registry System: Diethyl 4-oxo-1,4-dihydro-3,5-pyridinedicarboxylate(74632-03-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 74632-03-4(Hazardous Substances Data)

Usage

General Description

Diethyl 4-oxo-1,4-dihydro-3,5-pyridinedicarboxylate, also known as ethyl 4-oxo-1,4-dihydropyridine-3,5-dicarboxylate, is a chemical compound commonly used as an intermediate in the synthesis of pharmaceuticals. It is a member of the dihydropyridine family and is typically used in the production of calcium channel blockers, which are drugs used to treat conditions such as high blood pressure, angina, and arrhythmias. Diethyl 4-oxo-1,4-dihydro-3,5-pyridinedicarboxylate is often synthesized through the condensation of ethyl acetoacetate with ethyl cyanoacetate, followed by reduction of the resulting diester. Diethyl 4-oxo-1,4-dihydro-3,5-pyridinedicarboxylate possesses a wide range of applications in the pharmaceutical industry and is crucial for the production of various medications that are used to manage cardiovascular diseases.

Upstream product

• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 17758-33-7 3-methyl-5-nitro-4(3H)-pyrimidinone 
• 122-51-0 orthoformic acid triethyl ester 
• 168200-67-7 diethyl 1,5-bis(dimethylamino)-3-oxopenta-1,4-diene-2,4-dicarboxylate 
• 290-87-9 1,3,5-Triazine 

Downstream Products

• 244638-43-5 diethyl 4-chloro-3,5-pyridinedicarboxylate 
• 244638-44-6 ethyl 3-oxo-2-phenyl-3,5-dihydro-2H-pyrazolo[4,3-c]pyridine-7-carboxylate 
• 244638-45-7 3,5-dihydro-3-oxo-2-phenyl-2H-pyrazolo[4,3-c]pyridine-7-carboxylic acid 
• 1350912-63-8 5-amino-1-benzyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid 
• 1325297-17-3 1-benzyl-5-(1-benzyl-5-(tert-butoxycarbonylamino)-4-oxo-1,4-dihydropyridine-3-carboxamido)-4-oxo-1,4-dihydropyridine-3-carboxylic acid 
• 1325297-16-2 ethyl 1-benzyl-5-(1-benzyl-5-(tert-butoxycarbonylamino)-4-oxo-1,4-dihydropyridine-3-carboxamido)-4-oxo-1,4-dihydropyridine-3-carboxylate 
• 1325297-15-1 C₁₅H₁₆N₂O₃ 
• 1325297-14-0 1-benzyl-5-(tert-butoxycarbonylamino)-4-oxo-1,4-dihydropyridine-3-carboxylic acid 
• 1325297-13-9 ethyl 1-benzyl-5-(tert-butoxycarbonylamino)-4-oxo-1,4-dihydropyridine-3-carboxylate 
• 1325297-12-8 1-benzyl-5-(ethoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid 
• 1325297-29-7 methyl 1-benzyl-5-(1-benzyl-4-oxo-5-(2,2,2-trifluoroacetamido)-1,4-dihydropyridine-3-carboxamido)-4-oxo-1,4-dihydropyridine-3-carboxylate 
• 1325297-19-5 methyl 1-benzyl-5-(1-benzyl-5-(tert-butoxycarbonylamino)-4-oxo-1,4-dihydropyridine-3-carboxamido)-4-oxo-1,4-dihydropyridine-3-carboxylate 
• 1325297-59-3 ethyl 1-benzyl-5-(1-benzyl-5-(1-benzyl-5-(1-benzyl-5-(tert-butoxycarbonylamino)-4-oxo-1,4-dihydropyridine-3-carboxamido)-4-oxo-1,4-dihydropyridine-3-carboxamido)-4-oxo-1,4-dihydropyridine-3-carboxamido)-4-oxo-1,4-dihydropyridine-3-carboxylate 
• 1325297-18-4 C₂₈H₂₆N₄O₅ 

Relevant articles and documents

Five-fold-symmetric macrocyclic aromatic pentamers: High-affinity cation recognition, ion-pair-induced columnar stacking, and nanofibrillation

Described in this study is a conceptually new class of five-fold-symmetric cavity-containing planar pentameric macrocycles with their interior decorated by five convergently aligned, properly spaced carbonyl oxygen atoms. These cation-binding oxygens enclose a hydrophilic lumen of 2.85 A in radius and thus display high-affinity binding toward alkali metal cations, and possibly many other cations, too. Arising from their high-affinity recognition of metal ions, these planar macrocycles form cation- or ion-pair-induced one-dimensional columnar aggregates, and subsequently fascinating fibrillation results.

Synthesis of N-modified 4-aminopyridine-3-carboxylates by ring transformation

3-Methyl-5-nitropyrimidin-4(3H)-one reacted with enaminones to cause the ring transformation leading to functionalized 4-aminopyridines. Various kinds of amino groups can be introduced at the 4-position by modifying the enaminones. The modification of its vicinal positions was also possible. In addition, a bicyclic pyridine could be synthesized by making use of the vicinal functionality of a 4-aminopyridine-3-carboxylic acid. Georg Thieme Verlag Stuttgart.

Synthesis and transformations of alkyl 1,5-bis-(dimethylamino)-3-oxopenta-1,4-diene-2,4-dicarboxylates. A simple synthesis of dialkyl 1-substituted 4-oxo-1,4-dihydropyridine-3,5-dicarboxylates

Dimethyl (2a) and diethyl 1,5-bis(dimethylamino)-3-oxo-penta-1,4-diene-2,4-dicarboxylate (2b), available in good yields from the corresponding dialkyl acetonedicarboxylates (1a, b) and N,N-dimethylformamide dimethyl acetal (DMFDMA), were used as reagents for a one-step preparation of 1-substituted 1,4-dihydropyridin-4-ones (3a-u). Thus, compounds (2) were treated with ammonia, hydrazines, and primary aliphatic, aromatic, or heterocyclic amines to form dialkyl 1-substituted 4-oxo-1,4-dihydropyridine-3,5-dicarboxylates (3a-u).