69973-67-7

Upstream product

• 2227-79-4 benzenecarbothioamide 
• 93-91-4 1-phenylbutan-1,3-dione 
• 55-21-0 benzamide 
• 100-46-9 benzylamine 
• 56570-39-9 (2Z)-3-(benzylamino)-1-phenylbut-2-en-1-one 
• 98732-87-7 E-3-Oxo-1-phenyl-1-butenylphosphonsaeurediethylester 
• 54001-18-2 4-methyl-2-phenyl-thiazole-5-carbonyl chloride 
• 71-43-2 benzene 

Downstream Products

• 69973-82-6 2,6-diphenyl-selenolo[3,4-d]thiazole 
• 69973-77-9 2,6-diphenyl-thieno[3,4-d]thiazole 
• 69973-72-4 (4-bromomethyl-2-phenyl-thiazol-5-yl)-phenyl-methanone 

Relevant academic research and scientific papers

An efficient, one-pot, regioselective synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles under solvent-free conditions

In this article, we present an efficient, one-pot regioselective approach towards the synthesis of 2-aryl/hetaryl-4-methyl-5-acylthiazoles obtained during the reaction of α-bromo-1,3-diketones generated in situ by triturating unsymmetrical 1,3-diketones with N-bromosuccinimide, with various thioamides under solvent-free conditions. This environmentally benign protocol showed large functional group tolerance, resulted in the exclusive formation of a single isomer, out of the two possible regioisomers in admirable yields. The structure of the isomeric thiazole was assigned unambiguously on the basis of multinuclear NMR [(1H-13C) HMBC, (1H-13C) HMQC, (1H-15N) HMBC] and X-ray crystallographic studies. The entire protocol is ecologically desirable as it employs no organic solvent.

Iron-Catalyzed Synthesis of Substituted Thiazoles from Enamines and Elemental Sulfur through C?S Bond Formation

An atom economical approach for the synthesis of substituted thiazoles starting from enamines and elemental sulfur through the C?H functionalization/C?S bond formation is described. Under the optimized conditions, various substituted enamines reacted smoothly with elemental sulfur and the desired substituted thiazoles were generated in moderate to excellent yields. (Figure presented.).

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.