32623-28-2

Upstream product

• 2010-06-2 2-Amino-4-phenylthiazole 
• 68-12-2 N,N-dimethyl-formamide 
• 78587-78-7 5-Formyl-4-phenyl-2-(N',N'-dimethylformamido)aminothiazole 
• 89021-02-3 <(2-Amino-4-phenyl-5-thiazolyl)hydroxymethyl>phosphonsaeure-diisopropylester 
• 70508-79-1 (E)-3-Oxo-3-phenyl-1-propenyl-phosphonsaeure-diisopropylester 
• 84542-96-1 trans-1,2-Epoxy-3-oxo-3-phenylprop-1-ylphosphonsaeurediisopropylester 
• 89020-99-5 (3-Benzoyl-oxiranyl)-phosphonic acid diisopropyl ester 
• 1210051-67-4 2-[(1E)-1-aza-2-(dimethylamino)vinyl]-4-phenyl-1,3-thiazole-5-carboxaldehyde 

Downstream Products

• 1210051-75-4 [(2-amino-4-phenyl-1,3-thiazol-5-yl)methylene]methane-1,1-dicarbonitrile 
• 89021-12-5 N-[(5-formyl-4-phenyl)-1,3-thiazol-2-yl]acetamide 

Relevant academic research and scientific papers

A NOVEL AND VERSATILE SYNTHESIS OF HETEROCYCLIC ALDEHYDES USING DIALKYL 3-OXO-1-ALKENYL-PHOSPHONATES.

Dialkyl 1,2-epoxy-3-oxoalkyl-phosphonates, easily prepared from the corresponding 1-alkenyl-phosphonates, react with ambident nucleophiles to dialkyl 1-hetaryl-1-hydroxymethyl-phosphonates, which can be transformed to heterocyclic aldehydes.

Synthesis, characterization, and biological activity of substituted thiazole-5-carboxaldehydes and their ylidenenitriles derivatives

The Vilsmeier-Haack reaction of 2-amino -4-(4-substituted phenyl)-thiazoles 1, in the presence of micellar media, gives formylated derivatives 2, which upon hydrolysis afforded thiazole-5-carboxaldehydes 3. Microwave-assisted Knoevenagel condensation of 3 with active methylene compounds, in the presence of piperidine as catalyst, gives excellent yields of ylidenenitrile compounds 4. The structures of the newly synthesized compounds were established on the basis of elemental analysis, IR, 1H NMR, and 13C NMR spectral analysis. All newly synthesized compounds were screened for antibacterial activity using two Gram-positive and one Gram-negative bacterial species and their antifungal activity was screened using two fungal species. Taylor & Francis Group, LLC.

Dialkyl (1,2-Epoxy-3-oxoalkyl)phosphonates as Synthons for Heterocyclic Carbonyl Compounds: Synthesis of Acyl-Substituted Thiazoles, Indolizines, Imidazopyridines and Imidazopyrimidines

Dialkyl phosphonates (1) react with H2O2/Na2CO3 to give the corresponding trans-1,2-epoxy derivatives 2.These, on reaction with thioamides 4-7, afford (1-hydroxy-1-thiazolylalkyl)phosphonates 8-11, with ethyl α-pyridylacetate (indolizinylalkyl)phosphonates 19, with 2-aminopyridine (imidazopyridinylalkyl)phosphonates 20 (together with the α-amino compounds 22) and with 2-aminopyrimidine the (imidazopyrimidinylalkyl)phosphonates 21.On treatment with alkali or by pyrolysis the (1-hetaryl-1-hydroxyalkyl)phosphonates 9-11 and 19-21 yield the corresponding acyl-substituted heterocycles (thiazoles 13-15 and bicyclic acyl compounds 23-25). - The structure of the bicyclic derivatives 19-25 is assigned from the considerable deshielding of their 5-H NMR signals caused by the electron-rich substituents in peri-3-position.Condensation of the epoxyketones 2 with cytosine results in the isomeric (imidazopyrimidinylalkyl)phosphonates 27 and 28, which can be cleaved to the corresponding aldehydes 29 and 30, respectively.

Formylation of Some Heterocycles : An Application of Vilsmeier-Haack Reaction

Formylation of 2-amino-4-phenylthiazole, N-phenylthiohydantoin and 2-methylbenzimidazole by POCl3-DMF yields 5-formyl-4-phenyl-2-(N',N'-dimethylformamido)aminothiazole (I), N-phenyl-4-formyl-5-chlorothiohydantoin (III) and 2-(2-benzimidazolyl)-malonaldehy