4.5- Dialkyl-2-aminothiazoles

Dyatlova (193) reports the preparation of product 49, resulting from the dialkylation of 2-aminothiazole with a-chloroacetic acid under mild conditions (Scheme 36). 

N-(2-thiazolyl)dithiocarbamates are prepared by the action of carbon disulfide on 2-aminothiazoles (see Section III.3.C and Ref. 505). When refluxed with secondary amines these heterocyclic dithiocarbamates yield l,T-dialkyl-3-(2-thiazoIyI)thioureas (261) (491). 

The N,N-disubstituted thioureas (135) condensed with a-halocarbonyl compounds give 2-disubstituted aminothiazoies (136) but in lower yields (30 to 70%) (Scheme 65 and Table 11-20) (518). For example, N,N-dialkylthioureas condensed with chloroacetaldehyde or dibromoether lead to Ar,At-dialkyl-2-aminothiazoles in 136, Ri=R2 = methyl (342, 404, 436, 637), ethyl (343, 436), n-propyl (518), n-butyl (518), ally] (518), and benzyl (26, 29). When chloroacetone and dichloroacetone are the carbonyl reactants the corresponding 4-methyl (518) and 4-chloromethyl derivatives (572) were obtained. 

Aminothiazoles, with trinuclear Os clusters, 6, 730 Amino(triamido)-pentamethylcyclopentadieny complexes, with thorium and uranium, 4, 208-209 Aminotroponiminato ligands, in Ti(IV) dialkyl complexes,... 

Donthiri RR, Pappula V, Adimurthy S et al (2013) Sodium hydroxide catalyzed W-alkylation of (hetero)aromatic primary amines and Nl, C5-dialkylation of 4-phenyl-2-aminothiazoles with benzyl alcohols. J Org Chem 78(13) 6775-6781... 

---

See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

---