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 info for Chemistry of Heterocyclic Compounds: Thiazole and its Derivatives, Part Two, Volume 34
Aminothiazoles and their Derivatives 22 n -+ T * transitions have never been reported; they may be hidden by the absorption band related to the 7~ -+ T * transition. 2-p-R-Aryl-4-amino-5-benzoylthiazolesabsorb in the region of 389 nm ( E = 12,000), and the influence of R substituents on the band position was determined: R = MeO, A = 395 nm; R = NMe,, A = 429 nm (49,50). Table VI-2 contains representative ultraviolet data for 2-aminothiazoles and 2-iminothiazolines. r symmetry mainly located on C-5 and N-3: the “weights” of the atomic orbital in this MO TABLE VI-2.
Y (205) as summarized in Scheme 40. The important point is that in corxentrated sulfuric acid even dealkylation may take place: 56 457. Me. MexANapr MkJ\NwR ’ Me, Et-C McElCHOH 58 H’ 59 Scheme 40 All the examples of reactivity in acidic medium (Scheme 40) involve a reagent with a sp3C hybridized electrophilic center, but the actual reactive species generated bears a sp2C electrophilic center. 2). Thus the reactivity of 2-aminothiazole derivatives toward reactants bearing a sp3C hybridized electrophilic center follows the general pattern: 1.
Me XJ. Scheme 70 102 Chlorothioformic phenyl ester (103)reacts under mild conditions with 2-arninothiazole to give 104 (Scheme 71) (266). cl + PhOCSCl 2-% G N H C O P h NHZ II 103 Scheme 71 104 S 52 Aminothiazoles and their Derivatives b. REACTIONS WITH ACIDS AND THEIR ANHYDRIDES Acetic anhydride and sodium acetate when heated with 2aminothiazole for 2 hr give 2-acetamidothiazole 105 (Scheme 72) (243). Scheme 72 105 Quantitative studies of solid-state organic reactions were performed by Glazman (267, 268).
Chemistry of Heterocyclic Compounds: Thiazole and its Derivatives, Part Two, Volume 34
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