2-Amino-5-acylthiazole derivatives and synthetic method thereof
A synthesis method and technology of acylthiazole, which is applied in the field of 2-amino-5-acylthiazole derivatives and their synthesis, can solve the problems of high production cost, unfavorable operation, complex synthesis process, etc., and achieve low investment, easy operation, low cost The effect of wide adaptability
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[0032] In a second aspect, the present invention provides a method for synthesizing 2-amino-5-acylthiazole derivatives with a structure as shown in formula (I), comprising the following steps:
[0033] In an inert gas atmosphere, in the presence of a reaction solvent and a catalyst, the β-acyloxy enamine compound shown in formula (II) reacts with sulfur and cyanamide,
[0034]
[0035] Among them, R is selected from C1-C12 straight chain, branched chain, cyclic alkyl or alkenyl, substituted or unsubstituted C6-C12 aryl, or substituted or unsubstituted nitrogen atom, oxygen atom and sulfur atom At least one heterocyclic group of .
[0036] Concrete reaction steps are:
[0037]
[0038] Preferably, in the substituted C6-C12 aryl and substituted heterocyclic groups, the substituents are selected from halogen, methoxy, trifluoromethyl, trifluoromethoxy, nitro, phenyl, ester, carboxyl , amino, sulfone, hydroxyl and C1-C4 straight chain, branched chain alkyl.
[0039] In th...
Embodiment 1-27
[0049] Add β-acyloxy enamine compounds (see Table 1 for specific substances), sulfur powder, cyanamide, catalyst (see Table 1 for specific substances) and reaction solvent (see Table 1 for specific substances) in the reaction vessel, fill inert Gas (see Table 1 for specific substances); the reaction vessel is evenly heated to the temperature described in Table 1, and the β-acyloxy enamine compound, sulfur powder and cyanamide react in the reaction solvent, and continue to Said time; after the reaction, cool to room temperature, use ethyl acetate to extract the reaction solution, remove the solvent by rotary evaporation under reduced pressure, and then separate and purify by column chromatography to obtain the target product.
[0050]The concrete substance of β-acyloxyenamine compound, catalyst, reaction solvent, inert gas in the embodiment 1-27 of table 1, the molar ratio of β-acyloxyenamine compound, sulfur powder, cyanamide and catalyst, Reaction temperature and reaction tim...
Embodiment 1
[0058] The nuclear magnetic data of embodiment 1 product is as follows:
[0059] 1 H NMR (600MHz, CDCl 3 )δ5.88 (s, 2H), 7.49 (t, J=7.8, 2H), 7.56-7.59 (m, 1H), 7.64 (s, 1H), 7.78-7.8 (m, 2H); 13 C NMR (151MHz, CDCl 3 ) δ 187.02, 173.44, 149.01, 138.10, 132.15, 130.56, 128.65, 128.59.
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