Aminothiazoles and Their Derivatives (R. Barone et al.).
Mercaptothiazoles, Hydroxythiazoles and Their Derivatives (C. Roussel et al.).
Chapter VI Aminothiazoles and Their Derivatives (pages 9–368): R. Barone, M. Chanon and R. Gallo
Chapter VII Mercaptothiazoles, Hydroxythiazoles and Their Derivatives (pages 369–560): Christian Roussel, Michel Chanon and Rene Barone
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Extra resources for Chemistry of Heterocyclic Compounds: Thiazole and its Derivatives, Part Two, Volume 34
43 44 Scheme 32 With the more acidic 2-acetamido-4-R-thiazoles, using the weaker base NaOH as condensation agent, a mixture of ring (45) and exocyclic N-alkylation (46)may be observed (Scheme 33) (121). Reaction of 2acetamido-4-methylthiazole in alcoholic sodium ethoxide solution with a variety of alkylating agents has been reported (40-44). Use of aprotic solvents increases the quantity of exocyclic N-alkylation; the potassium salt of N-(2-thiazolyl)carbamate heated in DMF with 2phthalimidoethyl bromide gives predominantly exocyclic N-alkylation (70% 47a, 30% 47b) (Scheme 34) (131).
This reaction is 111. Nitrogen Reactivity 35 used to obtain tertiary thiazolyl amines (Scheme 30). 3) however is, more commonly used. LK NHEt + PhCH2Cl % cx ,CH2Ph N\ 41 Et Scheme 30 Similarly, coupling 2-aminothiazole with 2-dimethylaminoethylchloride in the presence of sodium amide yields 2-(2-dimethylaminoethylamino)thiazole (42) (186,187). LJi NHCH,CH,N(CH,), 42 Scheme 31 Reaction of 2-aminothiazole with P-phenethylchloride in anhydrous pyridine is reported to yield 76% 2-(p-phenethylamino)thiazole (43), the remaining 24% could be 2-hino-3(&phenethylamino)-4-thiazoline (44) (Scheme 32) (188).
118 ( 5 compounds, A), 109 (10 compounds, A), 89 (2 compounds, A), 1568 (A,B). A and B see Table VI-2. Intensities indicated by VS, very strong; S, strong; M, medium; sh, shoulder. v, stretching; 6, in plane deformation; y, out-of-plane deformation. A. Bands whose intensities depend on dilution. The typical infrared frequencies of a set of 2-imino-4-thiazolines were recently reported; however, their complete assignment is still to be made (101, 107, 122). Intensities of the deformation vibration band near 1600 cm-' plotted for 2-aminothiazole and other 2-substituted thiazoles versus the Hammett constant give a linear relationship (123).
Chemistry of Heterocyclic Compounds: Thiazole and its Derivatives, Part Two, Volume 34